I listened to Pete Holmes’s podcast, You Made It Weird, long before I ever watched his standup. Because as much as I love standup comedy, I love podcasts by standup comedians in equal measure. If it’s a comedian interviewing another comedian, even better. As a writer, I have always loved listening to others discuss their creative processes, and comedy has been a longtime favorite art form of mine. Enter You Made It Weird, where Pete has (often quite lengthy) discussions with comedians, actors, writers, and the like about life, but particularly about comedy, sex, and God.

The conversations are usually funny, but sometimes very serious and emotional. And what I love the most about the podcast is how vulnerable and open Pete is. While listening to him talk to countless other artists, his listeners have really gotten to know Pete in a way that feels more intimate than just a comedian-observer relationship. I know specific details about Pete’s childhood and relationship with his parents, how his divorce went down, how his views on religion and God have evolved over the years, and how he found his way as a comedian and ultimately was able to create Crashing, his HBO series based on his real-life experiences.

When I saw the trailer for Crashing, I felt a weird sense of pride, as if someone I knew personally had achieved their dream and I was getting to watch and cheer them on. This is what makes Pete so damn endearing and the main reason I love Crashing so much. He brings that same sense of openness to his character (himself), and it’s so easy to root for him. But Crashing is good for so many other reasons.  

Minor spoilers to follow.

Dating, Relationships, and Marriage

The series begins with the end of Pete’s marriage, and damn, it’s funny. When he’s blindsided by his wife Jess (played perfectly by Lauren Lapkus), sleeping with a free-loving art teacher/hippie named Leif (George Basil), Pete’s world is turned upside down. He leaves his marital residence with nowhere to go except into the city to try to get some stage time. You can imagine how performing the day you find out your wife is cheating on you goes...

As sweet, innocent, assumes-the-best-in-everyone Pete makes his way around NYC meeting comics and crashing on couches, he attempts to make sense of his split from Jess. Witnessing this very late coming-of-age solidifies Pete as a loveable, if bumbling, character who you just want to hug. But also shake.  

While Season One is pretty heavily focused on the Pete/Jess/Leif situation, Season Two sees Pete dipping his toes into the world of dating (and hooking up!). Watching a grown man who’s only slept with his ex-wife have his first one-night stand turns out to be one of the funniest moments of the show when he just won’t leave her apartment in the morning.

When Pete and Ali start dating, there’s a fun juxtaposition of her self-assuredness and experience with his man-baby positivity that makes for some really great dialogue between the two of them. They also seem to be growing as comedians together, and it’s fun to see Pete coming out of his shell a bit and being supported by a romantic interest. Side note: Ali is played by Jamie Lee, Pete’s real-life ex-girlfriend who is also a hilarious comic and great writer. She’s my other favorite part of this show.

The mixed-up relationships in Crashing are a sweet reminder that things are weird out there in the dating world, and that sometimes the people you least expect to teach you things often come with the lessons you need to experience most.

A Peek into the World of Comedy

If you like standup comedy at all, you’ll love the hilarious way Crashing digs into the less glamorous parts of “making it” in that world. From “barking” on New York City street corners, to performing some embarrassingly awful sets, to the harsh realities of life on the road, Crashing follows Pete into some hilariously awkward situations. And while he’s so, so good at playing himself as a naïve and brand new comic, some of his best awkward/endearing moments come in his relationships and friendships with others.

Plus, you get to see great standup in nearly every episode. We get to watch Pete’s early, shaky performances alongside his fellow newbie comics at The Boston (shout-out to Aparna Nancherla, who plays Anaya, just because I love her!). There are several episodes with a taste of the alt-comedy scene, and there’s even a great roast battle near the end of Season Two. Yes, Jeff Ross, comedy’s resident Roastmaster, is definitely in the episode.

In addition to Jeff Ross, plenty of other fantastic standup comics play themselves in the show and come in and out of Pete’s life. I’m talking Sarah Silverman, TJ Miller, Dave Atell, Hannibal Burress, Bill Burr, and Whitney Cummings, just to name a few. And perhaps the most charming comedian relationship Pete has is with Artie Lang, who also plays himself. Pete’s sunshine-and-rainbows worldview starkly clashes with Artie’s nihilistic, hard-partying ways, but watching the two of them together is gold.

Another great thing about Crashing is that all the funny moments don’t come from the standup performances. They come from the situations Pete puts himself in, but you never feel like you’re laughing at his expense. You’re so on his side, and I bet you will also start to feel proud of him as he starts to understand himself better. Maybe you’ll feel how I felt when I saw the trailer.  

The first season is good, but the show really hits its stride in the second season. Binge it all now on HBO before Season Three. And if you like it at all, check out Pete’s podcast for more insight into the topics explored on the show. And to all my fellow Weirdos out there: Keep it crispy.