Comic Tom Segura Talks His Love For Hip-Hop And New Book, ‘I’d Like To Play Alone, Please’

Tom Segura comes from a long line of doctors. His family has contributed to a variety of fields in medicine: surgery, urology, opthalmology, infectious disease, anaesthesiology, obstetrics and more. From a young age, he always knew he’d become a doctor, too.

But, during his freshman year of high school, Segura and his father spent a day observing surgery at the Mayo Clinic in Jacksonville. After bearing witness to procedures on everything from gallbladders to testicles, the teen decided that he’d much prefer the life of a professional football player than a doctor. Fortunately for comedy fans, neither of those career paths panned out.

Today, the 43-year-old stand-up has a slew of specials and albums—you’ve probably seen his latest hours, Ball Hog (2020) or Disgraceful (2018) populating the main menu on Netflix. He plays in clubs, theatres and arenas around the world, sharing the stage with titans like Dave Chappelle and Joe Rogan.

His podcast network—YMH Studios—is home to a variety of massively successful shows: Your Mom’s House (co-hosted by his wife and fellow comic Christina Pazsitzky), 2 Bears 1 Cave (co-hosted by comic Bert Kreischer) and his own interview show, Tom Talks.

Yesterday, Segura checked another box on his list of accolades by publishing his first book, I’d Like To Play Alone, Please, a collection of essays available through Grand Central Publishing. The stories oscillate from autobiographical childhood tales to hilarious slice-of-life anecdotes with some of the biggest names in sports, like Mike Tyson and Serena Williams.

But perhaps the most interesting facet of Segura’s book is the in-depth breakdown of his love affair with hip-hop music. Much like his aspiration of entering the operating room, Segura career as a rapper also hit a dead end.

In one essay, he revisits some of the cringeworthy lyrics he penned in a childhood notebook. While his rhymes didn’t withstand the test of time, his enduring passion for music persisted and permeated all levels of his comedy career.

In his stand-up, Segura has recalled meeting his hero, Brooklyn rapper Big Daddy Kane. In his podcasting, you can catch him romanticizing the golden age of hip-hop or interviewing artists. And at one of his live shows, he may even bring out a surprise guest—like the legendary DJ Premier—to hype up the audience.

Below, we spoke with Segura about his new book, how his love of music has intersected with his life as a comedian and more.

Your new book, I’d Like To Play Alone, Please, is a collection of essays. You’ve had so many experiences, thousands of hours of podcasts out there—but how was it for you sitting down and actually putting some stories on paper?

I didn’t really realize the undertaking that it is to write one of these—and it’s not a long read. To me, when I see the book, I feel like the amount of work in it, that it should be 400 pages. I think we’re at something like 70,000 words. Jesus Christ! When you think about term papers, it’s obviously like a fraction of that. I was actually like, “What should I keep? What’s interesting? What is either insightful or funny that’s also fun for me to tell?”—especially in the written form.

I’m used to telling stories on a microphone or on stage. You feel much more vulnerable writing than you do talking. With writing, you realize it’s going to be interpreted however the reader puts it together. But, ultimately I’m glad that I did it. It’s a thrill that I got to do it.

The book has a whole section dedicated to your love for hip-hop. Before we dive into that, can you tell me about your recent string of shows with Gang Starr’s legendary DJ Premier?

I’ve been a huge Gang Starr fan as far back as I can remember—to the late 80s, early 90s. He and I met via social media. I could not believe that he was interacting with me. I had posted a photo in their hoodie or something. I didn’t tag him or anything like that, but he reposted it. That started a back and forth. After I had a little rapport with him, I was like, “Hey, when I do my New York shows, I’m gonna reach out to you.” And he was like, “I’m in!”

I was like, “What!? How is this possible?” The whole thing felt surreal. How could this actually be real life? He would be my top first choice for that—everybody else would be after. To go for your first choice— the cream of the crop—and have them be like, “Yeah, I’d love to!” That’s crazy. Every one of those shows felt like a special event. And the cool thing about that was it was unannounced.

You actually did a Tom Talks podcast where you interviewed him. In the beginning, he explained that he’s a big fan of your comedy and podcasts. Were you totally geeking out?

One thing I’ve found very consistently is that a lot of musicians listen to podcasts. A lot of podcasters and comedians—we don’t listen to podcasts—we listen to music. You get it, they do music all day so they want a departure from it. We podcast all the time, we want a departure from that. So I’ve met a lot of musicians where they’re like, “That’s what we listen to on our tour bus or backstage.”

You and your wife—comic Christina Pazsitzky—have also linked up with Panic! At The Disco’s Brendon Urie, that way too, right?

He reached out to us and he’s like, “I love the podcast.” Like, what!? We’ve had him on Your Mom’s House, we’ve hung out with him. But it’s funny, you never think when you do stand-up and podcasts that it’s gonna reach certain people. You always get stopped by UPS drivers and the valet—working class people. You forget that anyone can be listening to it. Sometimes I’m blown away that a doctor is like, “Yeah I was listening to the podcast today and I wanted you to know that that’s actually a medical condition…” What!? There’s doctors that listen to this s**t! It surprises me. But the thrill is definitely when people in music listen.

That’s very obvious in your book, I’d Like To Play Alone, Please, where you took time to explain your love for hip-hop and music, saying it was your lifeblood. Why was that so important to you?

It feels like an honest thing to do. Writing a book, I’m just gonna be open about what my origins and influences are. I realized that I listen to music all day: when I wake up, in the car, backstage. I have such vivid memories of being a little kid and loving beats and funk—that sound. The new thing at that time was hip-hop.

It was the mid to late 80s. It was evolving and I was bananas for it. And you do see it as, “Oh, this is made by a different culture.” You recognize it if you’re a white kid in the suburbs. Not all my friends were into it, that’s what stood out to me. It was the first time I really felt a sense of independence.

In the book, I lay out The Fat Boys, Run DMC—that was the start of it for me. Then it evolved and I got more into De La Soul and A Tribe Called Quest, it was socially conscious stuff—and the music and melodies sounded different. You could tell that the art form was evolving. I felt like I was discovering something when you’re supposed to discover it: at the start. I listen to new stuff and try to make a concerted effort to not be the old guy who’s like, “This new s**t sucks.” I get into a fair bit of it, but I’m definitely married to that era of 90s hip-hop.

As you described it, at one point you were living in a super white neighborhood and people were totally bewildered at you wearing a Public Enemy t-shirt. Did it really feel that polarizing?

I looked insane. That was in the suburbs of Minneapolis. I’m wearing my Fear of a Black Planet t-shirt and I still remember my teacher being like, “What is that!?” I’m like, “Oh you know, Public Enemy!” I didn’t even understand the context of what I was wearing or what that message was.

I was there for the switch from cassettes to CDs and the great thing about those CDs is you would open those pamphlets and they had every lyric. You’d listen to the whole album and be flipping the pages and memorizing lyrics. I just loved how aggressive it was. I think it’s the perfect transition into puberty for a young man. You’re looking for something aggressive. Some people gravitated towards Metallica or Pantera—headbanger type of s**t—but for me it was Public Enemy or Eric B. and Rakim. It felt like a punch in the mouth.

When I was young I was given random CDs by my sister. I listened to a lot of 112’s “Peaches and Cream.” Outside of hip-hop, you took a lot of musical influence from your family, too, right?

I had all that R&B s**t, too, I loved 112 and En Vogue and SWV. My dad loved Motown which is funny because he didn’t have anything cool about him really. None of his style choices are cool, but Motown is dope. So he’d have like 100 Motown CDs.

Then my mom, she would listen to old school latin stuff from the 50s and 60s. Then her siblings’ children—who are my cousins that are my age—they would listen to more modern latin music. I got a pretty good affection for that when I was a young teen, too. I still listen to latin music, I’ll even get into Brazilian bossa nova stuff, I like flamenco music—stuff in that Spanish world.

It’s funny to picture your dad—a hardened Vietnam veteran—grooving out to The Supremes…

He f**king loved Diana Ross, The Supremes, The Temptations, Jackson 5—all the Motown big time stuff from that era.

Then he would get married to—remember when Seal had #1 hits? He would get that CD, like “Kiss From A Rose,” and if you were in the car with him, as it would end, his finger would go forward and he’d hit repeat.

Then it would end and he would hit repeat, like a toddler. He would do that for any new song that he dug. And we’d be like, “This is like the 15th time we’ve heard this song today.” And he was just like, “Again.” It was f**king weird.

You mentioned that some of your childhood friends were into way different music than you were. Since you weren’t listening to bands like The Smiths, how did you do your research on rap music? Did you just go to the mall and pick random CDs?

It was going to the mall, keeping your ears peeled and Yo! MTV Raps. That was awesome as a kid. I don’t think I ever would miss it. I remember the episode where Fab 5 Freddy is on the set of Wu-Tang’s video for “Da Mystery of Chessboxin’,” off the album Enter The Wu-Tang (36 Chambers). I had never heard of them.

I wasn’t from the New York area, it wasn’t a thing yet. They hadn’t broken nationally yet. They were like, here’s nine dudes in this s**t! Seeing that video and hearing that sound you’re like, “Oh my god!”

When young people hear older folks talk about MTV and what it was, it really was a way you would learn about stuff. It was the best for a minute. Then it just became a reality TV channel, which I’m sure that’s all just tied to advertising obviously, but it was cool because you would discover things that way.

Did you go to any concerts growing up?

I did go to concerts, but I wouldn’t say I was a hardcore obsessed concertgoer. In Milwaukee there’s this thing called Summerfest. We lived in the suburbs and that was one of the first things I went to where you would see multiple bands. It was huge. I remember Arrested Development played and they were huge at the time—“Mr. Wendal” and all that.

Over the years I went to some other concerts—Lauryn Hill at the Hollywood Bowl, Willie Nelson, Clint Black, other country people. In college I went and saw what at the time was the biggest hip-hop tour ever: it had Jay-Z, DMX, Method Man and Redman.

How has it been intersecting the music world with all your comedy podcasts? You’ve interviewed everyone from Talib Kweli to Shaggy 2 Dope from Insane Clown Posse.

Oh, it’s the best. They’re typically the most fun guests. Especially to sit down and chat with somebody who you’ve spent hours and hours listening to their music. They’re usually surprisingly down to earth and you get to pick their brains about things you’ve always wondered. It’s a fun hang.

Sometimes interviews with musicians can get too stiff if they take themselves a bit too seriously. That’s why I love listening to comics talk to musicians, it feels like they bring out a different side of them.

For sure. And actors can too, even comedians can. One of my favorite things, I had Tommy Lee on. I was like, “What’s the best drug?” And he was like, “Oh, it’s definitely heroin.” [laughs] We just talked about that. I was like, “God, I wish I woulda tried it.” He was like, “It’s rad dude. So good.” And we just chatted about how much fun that was and how much the road was when Mötley Crüe was touring stadiums. That’s the s**t I want to talk to a rockstar about—not necessarily about how they wrote a song.

What other music interview moments have really stood out to you?

The cool thing about DJ Premier was that when I had him on the podcast, it was hearing the little stories that you don’t usually get. How he was in the studio with Biggie and they were making “Unbelievable.” It had been like 10 hours and Premier was like, “Okay man, I’m gonna wrap up. I’m gonna get out of here.” And Big was like, “Nah, I got it.” And he just went in there and did it. He was like, “What the f**k!?” Just off the top of his head.

Or hearing the story about “Devil’s Pie,” like how Canibus turned it down. I couldn’t believe it. So, Premier was leaving a studio and D’Angelo called him and was like, “I’m looking for a beat.” And he played it over the phone. So he drove across to the other studio and gave [D’Angelo] the beat that’s “Devil’s Pie.” Hearing those kinds of stories when you’re a real fan of someone, it’s exciting. You can’t stop smiling.

I’m also glad to see that your network is producing a podcast with rapper Danny Brown. That dude is a total maniac, right?

I’ve been saying this and I can’t emphasize it enough—how naturally funny that guy is. That dude makes professional comedian level observations and commentary. Seriously, he’s way funnier than most of the comedians I hang out with. It’s not even close. It’s so good. To get him to do a podcast, it’s a dream. He’s so f**king funny.

Last question: You and Bert Kreischer have a notorious dance skill feud. However, as you explained in your book, you recently suffered an insane injury while playing basketball. Will you return to the dance floor anytime soon?

The answer is yes but I haven’t tried anything too advanced. I’m getting into it real slowly. I’ve danced but it’s real entry level dance moves. I haven’t tried anything that I could possibly hurt myself doing. But, that will come soon.

Tom Segura’s new book, I’d Like To Play Alone, Please, is available now.

Follow me on Twitter at @DerekUTG.