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This is not a profile of the 
comedian Brandon Wardell. 
 
It is a story about 
trying to be a good stepdad, 
an iconic Chicago haunt, 
Alexandria Ocasio-Cortez, 
and (never) giving up the dream. 
 
 
 
 
 
 
 
 
 
 
Winter 2014  
 
It is the winter of 2014 and I am lost, both in an industrial corridor of 
Chicago and generally, in life.  
 
It has been almost three years since I got a graduate degree in journalism 
and I only have a handful of bylines. I wasted the Canadian work visa I got 
from going to grad school in Montr​é​al. A year ago, I moved back home to 
Milwaukee to take care of my grandma, who is now dead.  
 
As I wander through a desolate area between Bucktown and Lincoln Park, 
trying to find The Hideout, I think about m ​ y grandma​—​a hard-working 
immigrant who came to Wisconsin from Ecuador in the 1950s​—​and how 
disappointed she was with the aimless globetrotting and underpaid 
freelancing that has characterized my young adulthood thus far.  
 
The cold-ass, end of February, Chicago wind pummeling my face feels like 
mi​ ​abuelita​ trying to slap some sense into me from the great beyond. 
 
⇆⇆⇆ 
 
The summer before, journalistic curiosity brought me to Detroit.  
At the time, the city was filing for bankruptcy and Michael Bay was 
shooting ​Transformers: Age of Extinction​ in downtown, transforming it to 
look like a Chinese city, which is ironic as hell. The trip yielded an 
8,000-word piece​ that I was not able to sell and​ that ended up o​ n my blog, 
like most things from my early writing “career.” 
 
The trip to Detroit also turned me onto a band called The Hounds Below, 
which was led by Jason Stollsteimer, who is best known for fronting  
The Von Bondies​—​they had that 2004 hit “C’Mon C’Mon”​—a​ nd for getting 
punched in the face by Jack White.  

1
The Hounds Below are playing The Hideout this winter night in 2014.  
I have never heard of the place, but apparently it is a Chicago institution 
that dates back to 1934.  
 
As Throop Street turns into Wabansia Avenue, The Hideout appears like a 
mirage in the desert. But, you know, a frozen-ass desert.  
 
The Hideout is a two-story, 18th century house smack dab in the middle of 
factory buildings. It kind of reminds me of Detroit, except in “the D” there 
would be a single house and literally nothing else around it, save some 
overgrown grass and cracked sidewalks.  
 
The Hideout is more than a cozy bar-slash-storied venue. It is a spiritual 
center. It is a monument to a time when America still cared about poetry 
and protest songs. It is an oasis.  
 
Unfortunately, in the not-so-distant future, The Hideout will sit in the 
shadow of a multi-billion dollar residential and commercial development 
known as Lincoln Yards.  
 
This does not surprise me. Late capitalism is an unrelenting wave, crashing 
down all around us. Blighted industrial areas become playgrounds for the 
rich. Lincoln Yards will become Dumbo on the North Branch. 
Gentrification is the new normal.  
 
This winter night in 2014, as I drunkenly sway and sing along to the overly 
earnest ballads of another indie rock band that will be lost to the annals of 
time, what I cannot foresee is that in four years I will return to The Hideout 
as the guardian of a teenage boy, to see the comedian Brandon Wardell. 
 
 
 
 

2
Christmas 2015  
 
It is Christmas morning 2015 and we are all together as a family under one 
roof—myself, my future fianc​é​e, her 10-year-old son and her 4-year-old 
daughter. We have been living together for a couple of months and dating 
for about a year, minus the month we split up because I freaked out over 
the prospect of life as a stepdad.  
 
It is now the boy who is freaking out. He has just unwrapped his big 
present, a brand new iPad. He is jumping and screaming and thanking us. 
His mom and I look at each other with naive satisfaction, unaware of how 
much drama the device will cause, how many new passwords we will have 
to create, and how many times he will have it taken away.  
 
The boy, like most of his generation—and ours—is helplessly addicted to 
technology. But it is not all selfies and games for him. More than anything, 
he craves information. Before the iPad he devoured books, magazines, 
anything he could get his hands on. The problem is that if a physical copy 
of the ​New Yorker​ is mid-grade weed, the iPad is pure heroin.  
 
Regulating a kid’s iPad time is a challenge I did not expect to face in my 
late twenties. On our first date, I told the boy’s mom that women had pretty 
much dictated my path up until that point and I was planning on breaking 
the trend. I said that my time in Milwaukee was limited and within a year I 
would probably be living in Ecuador. But then we fell in love. And now I am 
trying to make sure these kids eat their damn vegetables.  
 
Whenever we get into an argument with the boy about his abuse of 
technology, or about his lack of effort in school, I try to convey one simple 
idea: each day you wake up, you have a choice to either create or consume.   
 
 

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I am not saying that I expect him to produce a dope beat or write a 
hilarious sketch every day, but those are things he can do.  
 
Creation can be as simple as a conversation or a home-cooked meal. 
Putting down your phone or your iPad and letting your mind wander, 
letting thoughts form, that i​ s​ creation.  
 
People who make an effort to create on a daily basis tend to be happier than 
those who do not, regardless of the outcome, because the process of 
creation is rewarding in and of itself. 
 
For middle school boys, few concerns are more pressing than being cool.  
To this end, I try to communicate to the boy that being cool by virtue of 
consumption—like the clothes you wear—is tenuous, while being a creator 
is a far sturdier source of cool.  
 
Likewise, consumption is a costly and sketchy source of happiness. Not to 
mention, when consumption is your primary concern you are more likely to 
end up working a job you hate to maintain your paper chase.  
 
When it comes to being a creative professional, the boy’s mom and I are not 
as evangelical, because we are both struggling creatives—if you consider 
my freelance writing a creative endeavor.  
 
Nevertheless, we surround the boy and his sister with art and culture. We 
encourage and support their interests. We take them to see and do cool 
shit. 
 
Naturally, when the boy asks me to take him to see his favorite comedian, 
Brandon Wardell, at The Hideout in June 2018, of course I say yes. I even 
take it a step further. 
 
 

4
Spring 2012 
 
It is the spring of 2012 and I am holding a bag of bagels, standing at the 
base of One World Trade. The building has just become the tallest in New 
York City, though the spire will not be installed for another year. Across 
the street is the offices of the magazine ​Fast Company​.  
 
Like a dumbass, I sent a bunch of unsolicited pitch emails to magazine 
editors in an attempt to get the first thing I wrote out of grad school 
published. Not one of them garners a response, and I am positive not one of 
them is ever opened. And so, I have resorted to impersonating a bagel 
delivery guy to grab the ear of an editor.  
 
As you can imagine, security at the New York headquarters of ​Fast 
Company​—across the street from t​ he new World Trade Center​—is very tight, 
so I opt for plan B and head to Midtown Manhattan.  
 
⇆⇆⇆ 
 
A year earlier, I am sitting in my Magazine Writing class in Montréal. 
Graduation is right around the corner. We are worried about getting a job, 
because it is 2011 and journalism is—to put it lightly—in flux.  
 
Our professor does not attempt to assuage our concerns. Instead, he 
recommends that we start by writing about something that we love, 
because at least it will be a topic we should be familiar with.  
 
In the spring of 2011, that is comedy.  
 
Growing up in the 1990s, I inherited a love of sketch and stand-up from my 
dad. Then, coming of age during the George W. Bush years, comedy 
became essential. By 2011, I am regularly listening to comedy podcasts. 

5
 
Internet exclusive audio had been around since the mid 2000s, but the 
popularity of ​WTF with Marc Maron​ created a podcast boom in the early 
2010s that has resulted in virtually every single comedian having their own 
podcast today.  
 
That might sound kind of insane, but it has been great for comedians and 
their fans. Podcasting gives comics unprecedented control over their 
careers and it offers fans a treasure trove of content. This is a cultural 
development I felt was worthy of a feature story.  
 
And so, after finishing grad school, I set out to write about the genesis of 
comedy podcasting. I end up with a 4​ ,000-word piece​ that includes the 
voices of Marc Maron, Stephen Merchant, Scott Aukerman, Matt Belknap, 
Paul F. Tompkins, and other innovators of the burgeoning medium.  
 
⇆⇆⇆ 
 
As mentioned, I tried to get the story published in a major magazine. I 
thought it deserved to be in R ​ olling Stone​. But I do not know anyone in that 
office.  
 
After chickening out on the F ​ ast Company​ bagel delivery, I find myself 
trailing a bearded hippie onto an elevator and into the offices of ​High Times​.  
 
“Who ordered the bagels?” the secretary impatiently shouts, for the second 
time, into the adjacent room, where the employees of America’s best 
known cannabis culture magazine toil in cubicles more tidy than you might 
expect.  
 
You see, back in the day ​High Times​ covered a spectrum of counter-culture 
topics and I deluded myself into thinking they might again.  
 

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After about a minute of awkward silence, I confess my real intentions to 
the secretary. Amazingly, she does not kick me out, but escorts me into the 
office of an assistant publisher.  
 
This man is another bearded hippie, with long flowing white hair, cargo 
pants and a warm smile. He humors me for a few minutes before explaining 
why the story will not work for their magazine, namely because it has 
nothing to do with weed or Snoop Dogg or Willie Nelson.  
 
I end up giving away this story—that I worked on for like six months—to a 
comedy website based in San Francisco that has since been acquired by 
Vulture.com, a subsidiary of N​ ew York​ M
​ agazine​. It is shared on Twitter by 
Marc Maron and others, it does numbers, but I never see a dime. Sadly, this 
becomes a trend.  
 
Most of the things I write over the next couple of years are profiles of 
comedians like H ​ annibal Buress​, ​Maria Bamford​ and ​James Adomian​, that 
are published on websites based in Montréal, Toronto and New York City, 
which I am never paid for, though I do receive a press pass to the Montréal 
Just for Laughs Comedy Festival two years in a row.  
 
 
 
 
 
 
 
 
 
 
 
 

7
Summer 2018 
 
It is the summer of 2018 and my future stepson and I are about to be 
escorted onto the back patio of Chance the Rapper’s manager’s Wicker 
Park apartment by the comedian Brandon Wardell.  
 
When the 25-year-old walks through the front gate and introduces himself, 
the 13-year-old silently shakes his hand and eagerly nods his head. He is 
completely starstruck. 
 
⇆⇆⇆ 
 
In 2014, after moving back to Milwaukee, my writing begins to veer away 
from comedy and focuses more on music. In 2016, I am hired by W ​ isconsin 
Gazette​ to write a local music column and I start freelancing for the website 
of ​88Nine Radio Milwaukee​.  
 
However, I never stop listening to comedy podcasts. My (re)introduction to 
Brandon Wardell happens while listening to Howard Kremer and Kulap 
Vilaysack’s show ​Who Charted?​ On the episode Brandon loses his shit over 
a fire-ass Carly Rae Jepsen song. I am immediately on board. 
 
Turns out, that was not my introduction to Brandon. I actually saw him 
open for alt comedy icon and dramatic TV star Bob Odenkirk in November 
2014. I even ​wrote some nice things​ about his set. I attribute this lapse in 
memory to the fact that I was falling in love at the time.  
 
Whatever the case, Brandon’s show at The Hideout in 2018 presents an 
opportunity to earn some cool points and respect from the boy whose 
mother I love.  
 

8
The night the boy tells me that Brandon is playing The Hideout, I check 
their website to see if the show is all-ages. It says it is 21+. I call to see if 
they will make an exception. The person on the other end of the phone 
replies, “As long as you’re with him, it’s cool.”  
 
I reach out to Brandon’s people to see if he will be available for an 
in-person interview while in Chicago, with the angle being that the boy 
would join me and prepare some of his own questions. They oblige. 
 
As is my process, I do a deep internet dive and binge Brandon and Jack 
Wagner’s podcast ​Yeah, But Still​. I learn the basic biographical information 
that most fans should be familiar with​—Brandon was born in 1992, his dad 
was a troop, so the family moved around a lot, but he went to high school in 
the suburbs of D.C. His mom is from the Philippines and teaches Zumba. 
He has a little sister. Despite the relocations—he had the unfortunate luck 
of living in Alabama for seventh grade—Brandon, unlike most comics, 
comes from what appears to be a stable, happy home.   
 
Brandon seems to have got his edge online. As a kid, he spends a lot of time 
posting on internet forums. He becomes obsessed with baseball during the 
period when he lives in Washington state and Japanese superstar Ichiro 
Suzuki leads the Seattle Mariners.  
 
In middle school, Brandon takes pride in exclusively listening to novelty 
music by “Weird Al” Yankovic and Flight of the Conchords. In high school, 
he becomes a comedy nerd. He volunteers at a local festival where he meets 
headlining comics and is inspired to start performing. He does his first 
open mic at 17. He fumbles around so badly that the crowd thinks he is 
doing an Andy Kaufman-esque bit and it kills.  
 
 
 

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As a rising star in the D.C. comedy scene, Brandon visits Los Angeles to 
test the waters. Shortly thereafter, he drops out of college and moves across 
the country, arriving in L.A. during the same month of 2014 that I 
discovered The Hideout. His ascent in the L.A. comedy scene is swift.  
 
Bob Odenkirk taps Brandon for a tour and a live album recording. Brandon 
even appears on the cover of the record, which is like the alt comedy 
equivalent of being made by the mob. 
 
In 2015, Brandon’s online activity goes wild. Over the next two years or so, 
he averages 20 to 30 Tweets per day. He becomes known as a “millennial 
whisperer,” does some freelance writing, some on-camera work, becomes a 
Drake fanboy, tours with Bo Burnham, and continues to hone his stand-up.  
 
This period reaches its zenith in 2016 when Brandon popularizes the 
“Dicks out for Harambe” meme by making a Vine with the actor Danny 
Trejo. The six-second video catapults him to internet stardom and garners 
him a “Hot Comedian” w ​ rite-up in ​Rolling Stone​. It is at this time that my 
future stepson discovers Brandon.  
 
“Dicks out for Harambe,” like some of the best absurd internet phenomena, 
is eventually co-opted by the alt-right. Once this happens, Brandon and the 
University of Wisconsin-Milwaukee student who introduced it to the 
internet distance themselves from it. 
 
Listening to Brandon on his podcast, it becomes clear that he regrets much 
of his online activity during this time. He claims it was “fueled by manic 
depression,” and calls Twitter “a website that rewards mental illness,” a 
notion verified by the election of Donald Trump. 
 
 
 

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Brandon’s most memorable physical feature is his baby face, which serves 
him well when he is a hot young comic. By 2018, with his podcast taking off 
and his deleting of old Tweets, Brandon appears to be in the midst of an 
“adult rebrand”—a throwaway joke that seems to ring true.  
 
This is the angle I am thinking about working as we head into our 
interview with Brandon. I see myself writing a piece that might inspire my 
future stepson to do better at regulating his internet use. 
 
⇆⇆⇆ 
 
Sitting in Pat the Manager’s patio, the boy is clearly nervous. Brandon 
compliments his fit, which puts the boy at ease, though he refuses to ask 
his questions first.  
 
I start out by talking about the Montréal Just for Laughs Festival, which is 
the biggest comedy event in the world and the best attended by the 
entertainment industry. I ask Brandon about his audition for New Faces in 
2012 and whether he thinks the festival remains relevant. He says it is “no 
longer a be-all, end-all situation,” but he thinks it still matters. According 
to Brandon, comedians should focus on self-generating work. For starters, 
he suggests hosting a podcast and running a monthly stand-up show.  
 
When it’s the boy’s turn, he begins with a “Dicks out for Harambe” 
question. Brandon does a decent job of hiding his exasperation with the 
topic. He expresses regret, calling it “by far the dumbest part of my life.”  
 
The mood loosens considerably when the boy poses his second question. 
 
“What’s your favorite Soulja Boy Tweet?”  
 
Now t​ his​ is journalism. As Brandon begins to answer, he and the boy recite 
the Tweet verbatim in unison. My day has been made.  

11
The conversation shifts to the roots of internet rap and the immortality of 
Lil B, which reminds me of one of my favorite Brandon quotes.  
 
“Lil B’s influenced my comedy 100 times more than old ​SNL​.” 
 
After about a half-hour, we wrap up the interview and say our goodbyes.  
The next time we see Brandon he is onstage at The Hideout, working the 
sold out crowd with a mix of cheeky one-liners, wild characters, silly stories 
and funny observations culled from his eight years in the game.  
 
Despite claiming to be a retired aux cord DJ, Brandon re-emerges after a 
standing ovation for an impromptu aux cord set—complete with the Carly 
Rae Jepsen banger and the track “Chicago” by Sufjan Stevens, who happens 
to be Brandon’s favorite musician—plus a meet and greet with fans. The 
boy gets a picture and a quick chat with him.  
 
Later, the boy points out how Brandon made time for everybody in the 
room. Onstage, Brandon may be doing a send-up of toxic masculinity and 
awful Reddit subcultures, but offstage he is an absolute sweetheart.  
 
Since I began freelance writing almost ten years ago, one of my best friends 
has worked at T​ he New York Times​. Not once have I sent him a pitch, but 
that day in Chicago with Brandon inspires me to reach out. Brandon agrees 
to some follow-up phone interviews. After these conversations I put 
together a pitch and my friend at the ​Times p
​ asses it along to the 
appropriate editor.  
 
 
 
 
 
 
 

12
Fall 2014 
 
It is the fall of 2014 and I am in an Uber on my way to the opening night 
party of the Milwaukee Film Festival. I am o ​ n assignment​ for a local online 
publication. To be clear, the MFF might not have the prestige and star 
power of Sundance or Cannes, but it is, in fact, pretty badass. This is mainly 
due to the Oriental Theatre, a 1927 movie palace with East Indian decor 
that is hands down the best place to see a film in the Midwest—yes, better 
than anywhere in Chicago.  
 
Anyways, I am late to the party because I was just at the Pabst Theater, 
another Milwaukee gem, arguably one of the top ten venues in the nation, 
and where I will see Brandon open for Bob Odenkirk two months later.  
 
On this night at the Pabst I not only see Tim Heidecker and Eric Wareheim 
of the cult TV show ​Tim and Eric Awesome Show, Great Job!​, but also the 
amazing John C. Reilly in character as Dr. Steve Brule. I am riding high.  
 
Once inside the party, I grab a drink and sample what is left of the hors 
d’oeuvres. I do not see anyone I know except my boss at the online 
publication. He invites me to an afterparty at a nearby bar. I have missed 
the live bands. Not much is happening on the dance floor.  
 
I should mention that I am wearing a pastel colored floral baseball 
cap—backwards— and a burgundy velvet jacket. It is a wild fit.  
 
Within forty minutes of my arrival the party is over. We make our way 
down the stairs and out the door, where a red carpet awaits. It is on this red 
carpet that a beautiful brunette with red lipstick and a teal top turns to me 
and changes my life. 
 
“Are you my new BFF?” 

13
 
What an opening line.  
 
She invites me to a nearby bar. It is a different bar than the one my boss is 
going to, but I could care less. The bar that she and her friend take me to is 
very hip and very packed. I offer to get drinks. It takes forever. Eventually, 
she joins me in line. Lightning strikes. At the end of the night, instead of 
writing her number on my hand, she draws stars.  
 
At this point, it is only a matter of time.  
 
⇆⇆⇆ 
 
It is two months later and I am walking up to the same building where we 
met outside on the red carpet. The local university is hosting an interactive 
art exhibit at the building on this night. She is already there and she has 
company—her two little ones.  
 
I see the boy first. He is nine-years-old with shaggy hair and a black leather 
jacket. When his mom introduces me to him he is polite, as he is with all 
strangers, but he is guarded. I can sense his fear, anger, and apprehension. 
It will take us a couple of years to build trust.  
 
The girl is three-years-old. The severity of her parents split has not yet 
sunk in. She does not understand who I am or what I represent. I find her 
waddling down a hallway. With no hesitation, she gives me her hand.  
 
From that moment on we become best buddies. The transition from friend 
to father figure is bumpy and continues to require new approaches and 
adjustments, but damn, those first few months are bliss.  
 
 

14
Fall 2018  
 
It is the fall of 2018 and I am standing outside of a public high school in the 
most incarcerated zip code in America. In the past, driving through this 
Milwaukee neighborhood has prompted a drug dealer in a car to 
aggressively honk at me and ask “You tryna party?” Because why else 
would a young white guy be there other than to buy drugs? 
  
Today, I am in a line that stretches farther than I can see. It includes many 
white and black people. We are here because Barack Obama will be here.  
 
It is a week before the 2018 midterm elections. 
 
⇆⇆⇆ 
 
The first time I share the same air as Barack Obama is Election Night 2008. 
I am in Chicago, champagne drunk off my ass, a hapless recent college grad 
with a one-way ticket to London, a six-month U.K. work visa, and no real 
plans for my return to the States. 
 
I miss half of Obama’s victory speech outrunning a cop who spots me 
pissing in an underground parking structure. I make it back for the second 
half. When the speech ends the crowd explodes with joy and we parade 
down Michigan Avenue with the fullest of hearts.  
 
⇆⇆⇆ 
 
This time I have my shit together. I will not miss any of Obama’s speech. 
Waiting in line, I am reading C ​ hasing the Scream​ by Johann Hari. It is a 
phenomenal book about the global drug war. It is the kind of multi-year, 
multi-nation investigative journalism I can only dream about, because as a 
parent it would be tough to commit that much time and travel to a project.  

15
I sometimes feel like a phony when I call myself a parent. Sure, I live with 
the kids, I spend time with them, I care for them, I listen to them, their 
mom and I split rent and other expenses, but she​ does s​ o​ much more. She is 
an incredible mom and I simply follow her lead when it comes to parenting.  
 
⇆⇆⇆ 
 
When I was a kid I wanted to be famous, like, I suspect, most Americans. 
My plan was to go to New York University, study with Spike Lee and 
become a celebrated writer/director. I was going to make 
thought-provoking films that inspire social and political change, keep my 
integrity ​and​ make a lot of money, so I could give back, live comfortably, 
and help my parents retire early.  
 
I worked hard in school and was on track to get into NYU, but when it 
came time to go to college, I opted for the debt-free route of a nearby public 
university, courtesy of scholarships and my hard-working, blue-collar 
parents.  
 
That debtless freedom allowed me to get a work visa, which I used to live in 
Scotland and travel around Europe the year after undergrad. One country 
led to another, one career path led to another, and the dream was deferred. 
 
⇆⇆⇆ 
 
Don’t get it twisted though, I have always wanted kids. For whatever 
reason, when I was young and a girl would break my heart, I would 
daydream about traveling the world with my kid as a single dad, but I 
would have preferred a nuclear family. Later, after learning about 
overpopulation, systemic injustice, and the foster care system, I became 
open to adoption. 
 

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However, being a stepdad—especially when the biological dad is around 
and problematic—can be pretty frightening.  
 
Early on in our relationship, I read a Facebook post that scares me​. It is ​one 
of the those sharebait-y, who-knows-if-it’s-true posts​ about a stepdad who 
does everything for his stepdaughter, who pays for her wedding, but who is 
replaced at the last minute by her deadbeat bio-dad and does not get to 
walk her down the aisle.  
 
The message was clear—no matter how much you love them and care for 
them, you will never replace their biological dad.  
 
For someone with an admittedly outsized ego, that is a hard pill to swallow.   
 
⇆⇆⇆ 
 
Over the last five years, my f​ ianc​é​e​ has chipped away at that ego, and I am a 
better man for it. Slowly but surely, I have made sacrifices and prioritized 
my family. I have started to look more realistically at my freelance writing 
career, which has been subsidized by a substitute teaching job since I 
moved back to Milwaukee.  
 
While my writing career may be trending upwards in one sense​—​I have 
won multiple local awards, I have ​my first book​ coming out, I have 
interviewed some fascinating people like K ​ amasi Washington​, ​Giannis 
Antetokounmpo​, and ​Lauren Mayberry​—t​ here has been no financial 
windfall to match.  
 
The freelance pay rates I receive cannot support a family, or would require 
me to work so much that I would barely see my family. The full-time job I 
was offered by a publication that has since folded, the same paper whose 
ghost of a website you might be reading this on, paid less than substitute 
teaching. To top it off, the book project has left me in considerable debt.  

17
 
The fact is that journalism has been slowly bleeding out since the 
introduction of the home computer. Today, my local daily newspaper is 
barely enough kindling to start a fire. In January of this year alone, more 
than two-thousand people who write for the internet lost their jobs.  
 
Two days before the Obama event I get an email from my friend at T ​ he New 
York Times.​ The editor thinks the focus of my pitch is not there yet and is 
not convinced the timing is right, but offers feedback and says they are 
open to a re-pitch.  
 
⇆⇆⇆ 
 
During our first phone conversation, I ask Brandon what he thinks caused 
the “manic depression” that fueled his Tweet storm of 2015/2016. He gives a 
non-answer. He mentions the “quick high” he got from Twitter, which he 
no longer gets. I ask if reading books, which he is trying to do more of, is a 
conscious effort to counter his internet addiction. Another vague 
non-answer.  
 
I start to doubt the recovering internet addict/maturing comedian angle.  
I remember being the boy’s age and how much unregulated time I spent in 
AOL chat rooms and on Instant Messenger. I wonder if it is even fair to use 
Brandon’s story to teach the boy a lesson?  
 
⇆⇆⇆ 
 
Back at the high school, we make it through security and enter the 
gymnasium. The atmosphere is absolutely electric. Local singer L ​ ex Allen 
does a gorgeous rendition of the national anthem. The anticipation builds 
as each of the Wisconsin Democrats deliver their stump speech. When 
Obama finally takes the stage the crowd showers him with love. He is just 
as charismatic and inspiring as ever. 

18
Winter 2019 
 
It is the winter of 2019 and my fiancée and I are driving from Milwaukee to 
Columbia, Missouri. We are heading to the True/False Film Festival where 
she has been hired to work.  
 
My fiancée is a visual artist specializing in stage design and installation. 
This will be her fifth festival in the last year. They have taken us all over 
North America. At these events we are warmly welcomed by the local arts 
community, her “lofi magic” transforms a space and comes alive with 
music, lights, and energy, and we discover new art and new friends.  
 
These trips have fast become my favorite activity of all-time.  
 
It is the day of Michael Cohen’s congressional testimony. The hearing 
coincides perfectly with our drive to Columbia, so we listen to most of it. 
The best is saved for last. That is, questions from the freshmen members of 
Congress, chief among them being a 29-year-old Democrat from New 
York’s 14th district named Alexandria Ocasio-Cortez, better known as 
AOC. 
 
Her time is short. H​ er questions​ are smart. She is a star in the making.  
 
The next day, while my fiancée and I are in the middle of a marathon 
installation at the Blue Note Theater in downtown Columbia, AOC appears 
in front of us, 50-feet tall. It is the opening scene of the documentary K​ nock 
Down the House​, which follows four women who run for office in 2018.  
 
AOC is in a bathroom applying makeup and making a lighthearted point 
about gender inequality as it relates to fashion choices for politicians. We 
see this scene a few more times as the projectionist tests the equipment.  
 

19
The day after, we watch the entire film with a sold-out crowd. The moment 
AOC appears on screen the room erupts with cheers. By the time the 
credits roll, the theater is brimming with emotion. Director Rachel Lears 
receives a standing ovation before her Q & A.  
 
At this point, AOC may be known more for how much she is hated by the 
right than how much she is loved by the left. This, I think, is a sign of her 
power. She is so sharp, so charming, and so adept at social media that the 
right is deathly afraid of what she could become. 
 
It’s funny, older people think AOC is some kind of unicorn because she is 
good-looking, good at Twitter, and not afraid to challenge American 
exceptionalism, but she is similar to my peers. What sets her apart is that 
instead of being cynical and self-serving​—​like most of us​—s​ he had the guts 
to put skin in the game and join the circus.  
 
A popular criticism of AOC is her opposition to the deal that would have 
put a secondary Amazon headquarters in Queens. Her amplification of a 
grassroots movement against the deal helped put it to bed, which is used to 
paint her as a “job killer.” But AOC’s position on the Amazon deal was a 
principled stance rooted in her millennial brand of democratic socialism, 
which rejects massive government subsidies to companies that already get 
tax breaks, especially one that does not even pay federal income tax. 
 
The increasing appeal of socialism in America is a direct result of 
Reagan-era deregulation, which has allowed corporations to post record 
profits, pay out their CEOs at ever-increasing rates, receive government 
handouts and bailouts, all while undercutting the working class. 
Essentially, we have created a system that offers safety nets and socialism 
for corporations, while working people endure cut-throat capitalism. 
 
In 2020, Donald Trump will run on the supposed strength of the economy, 
but AOC reminds us that not all jobs are good jobs. 

20
Earlier in the winter of 2019, my fiancée and I are on a belated birthday 
getaway in Chicago. We are heading to The Hideout to see the comedians 
Patti Harrison, Mitra Jouhari, and Catherine Cohen.  
 
It is my fiancée’s first trip to The Hideout. Wabansia Avenue is wearing a 
thick coat of snow on this January night. It feels like we are walking in a 
snow globe as we trek to the venue. We enter the front door, shake off our 
boots and cozy up to the bar.  
 
“Oh my God, I l​ ove​ this place!” my fiancée exclaims. 
 
There is no opening act on the bill, but Tim Tuten, co-owner of The 
Hideout, takes the stage. He is feeling himself and popping off about the 
Lincoln Yards plan. He urges the crowd to join the fight against the 
development and to show up at the next city council meeting to express 
their opposition.  
 
The original plan for Lincoln Yards included entertainment venues to be 
run by Live Nation, which would have been devastating to The Hideout and 
other independent venues in town. These have since been eliminated, but 
the developers are still on track to receive significant tax breaks to build a 
mini-downtown that most locals do not want, which will primarily benefit 
the wealthy.  
 
Meanwhile, Chicago Public Schools is starved for funding.  
 
This is Gentrification 101.  
 
It is time we call gentrification what it is​—the pendulum of white flight 
swinging back from the suburbs to the cities. There may be some people of 
color moving into gentrified areas, but generations of institutionalized 
racism has kept communities of color from building wealth, so it is mostly 
young white people moving into neighborhoods their elders abandoned.  

21
Since I bought tickets to see Brandon Wardell at The Hideout in 2018, I 
have been receiving the venue’s email newsletter. The week before the 
birthday getaway I learn that the musician/comedian/video editor DJ 
Douggpound, best known for his editing work on T ​ im and Eric Awesome 
Show, Great Job!​, will be playing The Hideout in March. However, the show 
is at 10 p.m. on a school night.  
 
This is a bummer, because the boy and I would have to drive down and 
back from Milwaukee, which is a bit more than an hour north of Chicago. 
His mother is not down for this plan. Yet, I desperately want the boy to see 
Douggpound live, because Doug is a singular talent who combines many of 
the boy’s interests.  
 
The boy is a budding musician, producer and DJ, with great taste in 
comedy. No surprise, whenever we take the iPad, internet and video games 
away, his first instinct is to make music or silly graphics, which kind of 
makes us want to take those things away permanently. 
 
I reach out to Douggpound via email to see if he can swing a show in 
Milwaukee the same week as his Hideout gig. He replies that while he 
would like to, he agreed to a radius clause prohibiting such a show. 
 
⇆⇆⇆ 
 
While slightly drunk at the True/False Film Festival, a day after seeing the 
comedian Nathan Fielder’s film ​Finding Frances​, hours after seeing a talk 
with Tim Heidecker, and moments after walking into the VIP entrance of a 
club behind these two comic geniuses, I convince my fiancée to let me take 
the boy to see DJ Douggpound at The Hideout.  
 
 
 

22
Spring 2019 
 
It is the spring of 2019 and I am in front of a fourth grade classroom, 
reading a book about a hamster named Humphrey. Summer vacation is fast 
approaching. The students are antsy. Visions of swimming pools, bike 
rides, and staying up late dance in their heads. Most could care less about 
Humphrey. My mind is also distracted, because a h ​ igh-profile interview 
that I conducted the week before is set to publish within minutes, and I am 
trying to formulate what I will say about it on Twitter. 
  
Much of my time as a substitute teacher has been spent this way​—with my 
attention split between the students and my latest writing assignment. This 
does not make me the best substitute teacher, but I am not the worst either. 
I listen to the students, I help them out whenever I can, and I make it a 
point to connect with at least one student each day. But as a general rule, I 
seek out high school positions where the students will be able to keep 
themselves busy or at least not throw chairs at each other, so I can 
simultaneously get some of my own work done. 
 
In the last two years I have managed to land two long-term positions, 
which are much preferred to day-to-day subbing. Long-term gigs give you 
time to build relationships with students and actually teach them, instead 
of being treated like a subhuman babysitter.  
 
The fourth grade position comes a week after finishing one of these 
long-term gigs. It is jarring to be back at a day-to-day job. After getting the 
students started on their science research and posting my article on 
Twitter, I walk around the room, answering questions and offering 
guidance. Being on my feet and engaging with students feels much better 
than sitting at a computer and agonizing over my words. Getting out of my 
head and giving myself over to the students makes me feel whole.  

23
A couple years back, my fiancée quit her day job to become a full-time 
artist. It has not been easy for us. She too has had to subsidize her income. 
Walking to that fourth grade classroom I admire a series of farm animal 
paintings she did with K4 students as part of a residency.  
 
The reality is that running a household with the income of two struggling 
creatives is not sustainable. Sure, it is meaningful and our kids are 
continually inspired by her artwork and my writing, but that will not get us 
our own house with a driveway, a basketball hoop, a garden and a dog. It 
will not pay off her private art school debt. It will not allow us to visit my 
brother and his wife in England. It will not take away the anxiety she 
experiences every day​—w ​ ondering when the next festival job or school 
residency will come along so she can help out with groceries and pay rent.  
  
⇆⇆⇆ 
 
I walk out of the Obama event in the fall of 2018 with a full heart, much like 
Election Night 2008, but this time I also have a clear mind. I open my 
phone and respond to the email from my friend at ​The New York Times​. I 
tell him that I will not be sending the editor a new pitch. I am aware of 
what a ​Times​ byline would mean to my career. I am not prepared to head 
down that path​—​to accelerate the freelance struggle. Instead, I enroll in a 
program to become a licensed English teacher.  
 
I always saw myself becoming a teacher, but I thought it would be after a 
successful career as a writer/director. I have been haunted by the saying 
“Those who cannot do, teach.” I considered becoming a full-time teacher as 
equivalent to failure. 
 
Today I see it differently. I look at my family​—​at my incredibly talented 
fiancée, our strong-willed little girl and our brilliant teenage boy​—​and I 
realize that whatever I can do to help them succeed is the opposite of 
failure. I realize that I am happier when I live and work for others. 

24
⇆⇆⇆ 
 
When I get home from work the day the boy and I are going to Chicago to 
see DJ Douggpound, he is on the iPad. This is how I find him most days 
when I come home. With high school on the horizon, girls in the mix, and 
his image being his greatest concern, Instagram is now his primary 
obsession. The struggle continues. 
 
“Hey, grab your glasses, a snack and a water bottle, we’re going to The 
Hideout to see Douggpound,” I tell him. 
 
Usually when he is on the iPad and we talk to him, he acknowledges us 
without looking up. Not this time. 
 
“Whaaaat?….Okay!” 
 
The boy is ecstatic. We jump in my car and head south. I let him DJ the 
drive. We talk about music, sports, and a little bit about the future. He has 
so much life ahead of him.  
 
We make good time by Chicago traffic standards and arrive at The Hideout 
almost three hours before the show is scheduled to start. I suggest we pop 
in and check out the situation before going to grab something to eat. When 
we walk in the woman at the door asks for his ID and I tell her that he is 
fourteen and my stepson.  
 
“Ummm…” she stutters. 
 
“We’ve got tickets to the show later. I brought him to see Brandon Wardell 
last summer and it was all good,” I say. 
 
“Wait, you were at the show yesterday?” she asks. (Brandon played The 
Hideout the day before.) 

25
“No. Last summer. I called ahead and the person I talked to said it was 
cool,” I reply, starting to get nervous. 
 
“That was an early show,” says another woman from behind the bar. 
 
“I don’t think he can be at the show tonight. It says 21 plus right there on 
the website. Let me get the manager,” she adds. 
 
The boy and I look at each other. He is uncomfortable. I am embarrassed 
and angry. I can feel the rug being pulled out from under us. The manager 
walks in from the venue. He has already been briefed on the situation. 
 
“I’m really sorry. I understand you brought him last summer, but things 
have changed,” he says.  
 
“Man, but we drove down from Milwaukee just for this show,” I plead. 
 
At this moment, Brandon appears from behind the door that leads to the 
green room. Once again, the boy is starstruck. I am desperate. 
 
“Yo Brandon! Good to see you again man! Dude, we came to your show last 
summer and now they’re not letting the boy in tonight. What’s the deal?”  
 
What a sad, shitty move on my part. I regret it immediately. Part of me 
wonders if I had actually followed through on ​The New York Times​ profile 
would Brandon have stuck his neck out for us? I also wonder if The 
Hideout’s strict enforcement of the age limit has something to do with 
their public opposition to the Lincoln Yards development.  
 
Brandon does not engage with my plea. The boy steps in and makes 
friendly small-talk with him. The manager offers to refund the tickets in 
cash and throws in extra for gas. It is not a bad deal, but I still feel terrible.  

26
On the drive back to Milwaukee the boy keeps our spirits up. He is excited 
to have seen and talked to Brandon again. On our way out of the city we 
take a picture outside the Illinois Bone & Joint Institute, which we joked 
about being our reason for coming to Chicago on our drive in. We have 
dinner at a travel plaza. The boy is grateful for the meal and the impromptu 
trip, despite how it turned out.  
 
As we pass the Klement’s Sausage Co. factory and the Milwaukee skyline 
appears, I think about how this night is kind of emblematic of my life. 
Things have definitely not turned out the way I planned when I was the 
boy’s age, but I have had a lot of unexpected fun along the way.  
  
When I was 18, my goal was to be famous by 26, because that is when Kanye 
West broke big, and he was one of my heroes. Not to take anything away 
from his artistic accomplishments, but considering where Kanye’s 
ego-driven attitude has taken him these days, I am not sure he is the best 
role model. I now look to a different Chicago guy for guidance.  
 
It was during Barack Obama’s speech at the high school on Milwaukee’s 
near north side that I decided to become a full-time teacher.  
 
From the outside, it might look like I am giving up on my dream of being a 
writer/director. But the dream was always rooted in making a difference 
and inspiring positive change in the world. Now I realize that I can do that 
more directly by teaching and mentoring youth. I also realize it is a 
decision based on what is best for my family, what I am good at, and what 
satisfies my soul. Plus, I lost the desire to be famous. 
 
To be sure, I will never stop writing. I did not stop when I was living in 
Scotland and working temp jobs. I did not stop when I was working on a 
farm in Oregon. And I did not stop when I was in between Montr​é​al and 
Milwaukee, scraping together a life.   
 

27
⇆⇆⇆ 
 
It is a few days after being in the fourth grade classroom. My family and I 
are on a road trip to Canada where my fiancée will work at another festival. 
Our first stop is Detroit. We head straight to a DIY skate spot the boy 
knows about. 
 
The skate spot is located northeast of downtown. The neighborhood seems 
a bit sketchy, but so is almost everywhere in Detroit. My fiancée does not 
think it is a good idea to be there. The boy does not protest. I, however, 
insist that him and I check it out while the ladies stay in the car.  
 
There are a handful of adult skaters and a pair of preteen boys on bicycles 
at the spot. The boy does not hesitate to jump in. I sit on a log with a nice 
view of the action. There is graffiti on everything. The vibe is chill. It is a 
sunny day. There is even a place for the little girl to run around.  
 
After about five minutes I head back to the car. As I am walking, a black 
car pulls up and a skinny, grey-haired white guy gets out and grabs a 
skateboard from the trunk. 
 
“Look at this lame-ass suburban dad,” I think to myself. 
 
I jog down the hill. When I reach the sidewalk the man turns around. He is 
a few feet in front of me. We nod at each other and he smiles. I do a double 
take. 
 
I try to calculate in my head how many skate spots there are in the world. 
Indoor, outdoor, recreational, professional, municipal, DIY, all the 
backyard ramps and converted pools. I would guess there are well over a 
million, but I do not know much about skateboarding.  
 
 

28
However, I do know what Tony Hawk looks like.  
 
Of all the skate spots in the world, the most famous skateboarder on the 
planet just happened to swing by this one spot in Detroit on this one day, 
minutes after we arrived en route from Milwaukee.  
 
Very rarely do I cuss in front of the little girl, but when I get to the car I 
lean into the window and say, “It’s cool. There’s a log we can sit on and a 
place for her to play. Also, TONY FUCKING HAWK IS HERE.” 
 
I see the boy’s face light up the moment he realizes who the old guy is. 
Sitting on the log, Tony does a grind right in front of me and smiles just as 
he did when we first nodded at each other. Later, he watches the boy skate 
and gives him advice. 
 
Tony spends ten minutes or so trying to land this one trick. It seems pretty 
difficult, but then again, he is Tony Hawk. He gets frustrated with himself, 
but he is persistent. After one fall he does not get up for almost a minute. 
We all look at each other like, “Did we just see the end of Tony Hawk’s 
career? Are we going to have to take Tony Hawk to the hospital?”  
 
Tony gets up, eventually lands the trick, and we give him a round of 
applause. Before we leave the boy gets up the nerve to ask for a selfie. Then 
I see TONY FUCKING HAWK fix his hair as the boy readies the phone 
camera. What a way to start the road trip. It feels like a sign that we are on 
the right path. 
 
Then, a few days later, the boy and I take an Uber to a beach in Toronto, we 
dig our feet in the sand and we enjoy Vampire Weekend’s first show on the 
Father Of The Bride Tour​—​the boy’s surprise eighth grade graduation gift.  
 
It is foggy, overcast, and there will be patches of rain, but as I have found, 
the best concerts are in the rain.  

29
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
Look outside at the raincoats coming, say oh​. 
Hey, hey, hey, hey.

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