How Lexington’s Pete Holmes got Judd Apatow’s attention and became a comedy star
An affair ended the evangelical Christian’s marriage and made him question everything he lived by. But out of that wreckage came his hit HBO show, “Crashing,” and a new spirituality of sorts.
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Season 2 of the semiautobiographical HBO comedy Crashing opens with star Pete Holmes at the nadir of his postdivorce life. He is living in a cluttered garage, trying to suppress his pain by consuming unhealthy quantities of Chinese takeout and unholy amounts of porn.
In the first season of the show, viewers saw the Pete character get dumped by his wife, a fellow evangelical Christian he had met at Christian summer camp and married immediately following Christian college. The breakup came after he walked in on her with another man. They saw Pete, a lovably guileless transplant to New York from Boston, endure an existential crisis where he came to question all the truths that had served as the guardrails of his life. And they saw him try to convert his heartbreak into fuel for his drive to become a successful stand-up comedian. He had a long way to go. To get stage time, he had to spend hours handing out fliers, trying to entice unsuspecting tourists into a dingy Manhattan club called The Boston for weak sets and watered-down drinks.
In a sound editing session in October, Pete Holmes screens the first episode of season 2 (which has just started airing on HBO). The 38-year-old sits in the dark with his mentor and fellow executive producer, Judd Apatow, their yellow legal pads in front of them. They’re in Dubbing Stage 11 on the Sony lot in Culver City, California. In the cold open of the episode, as the camera lingers on a tight shot of Pete in the garage, inhaling greasy Chinese food, Apatow cracks, “Half of America turned it off when they heard your eating noises.”
“But they’ll stay for the masturbation!” replies Pete Holmes, the show’s creator, just before Pete Holmes, the lead character, moves his hand toward his lap.
I am seated behind them, and now Apatow glances back at me and quips, “This is the opening of the article in Boston: Pete sat in a sound room looking at himself masturbating.”
Not quite, but pretty close. I usually don’t take script notes from the people I’m writing about. But who am I to second-guess Apatow, the Hollywood producer and director with the proven gut for turning awkward sex into comedy gold?
It wasn’t the sex material that prompted Apatow to give Holmes the same kind of star turn he’s given other confessional creators like Lena Dunham, Amy Schumer, and Kumail Nanjiani. What attracted him most was Holmes’s other preoccupation: God.
“It’s a new way to discuss spirituality and religion through the world of comedy,” Apatow tells me. “What’s unique about Pete’s character is he’s a believer who’s very sincere about his faith and is trying to find a way to be a comedian but not lose his soul. That forces him to question it all because that’s what comedians do — they call bull on everything.”
Apatow is Jewish but, unlike Holmes, he wasn’t raised with any kind of religion. “I wanted to be bar mitzvahed, and my parents said to me, ‘No, you just want the money.’ They didn’t replace the spirituality with something else. So I always had a hole there. In my life I’ve been fascinated by it because, on some level, I feel empty and need to figure it out.”
As hilariously raunchy as Crashing can often be, its exploration of faith is what makes the show noteworthy. Sure, it’s fun seeing Pete pal around with bed-hopping, coke-snorting, atheism-spouting comics while losing and finding himself, a twentysomething evangelical’s version of an Amish teenager’s Rumspringa. Yet it’s hard to find another work of entertainment television that treats the searching side of spirituality as honestly and open-mindedly as Crashing does.
Evidence of this comes just 10 minutes after the noodles-and-self-chill opening scene. Pete meets magician Penn Jillette at a comedy club and quickly finds himself deep into a discussion about the meaning of life.
On what other comedy show could you witness a thoughtful back-and-forth between an atheist and an evangelical — both knowledgeable — that jumps from Leviticus to the inerrant word of God to Pascal’s Wager?
Pete: What if you die . . . and if you’re good, you go this way; and if you’re bad, you go to hell?
Penn: Isn’t that disrespectful to God and to Jesus, just to use them as an afterlife insurance policy?
Pete: So you don’t believe in something watching us, something keeping all of this going?
Penn: I’m not sure there’s no God, but I don’t know. The most important revolution in human history . . . is the scientific revolution, which came down to three words: I. Don’t. Know.
Pete: What if you’re wrong?
Penn: What if you’re wrong?
Pete: Either way, I’m good.
Penn: No, no, that’s not true. That’s the problem with Pascal’s Wager. There’s more than one choice. You could spend your whole life praying your ass off to Jesus and then find out that it’s actually Zeus and he doesn’t like your praying to Jesus.
The scene is compelling and provocative. What it isn’t, alas, is funny. When the lights come up in Dubbing Stage 11, Apatow zeroes in on this problem. “It felt a little preachy and long,” he says. “There’s like one laugh in it. How long is it?”
“3:29,” a sound engineer replies.
“Yeah, we should know what the 2:29 version looks like,” Apatow says, looking down at his legal pad. (Holmes, a talented cartoonist whose drawings have frequently been published in The New Yorker, has been using his pad mostly to sketch something resembling the Marlboro Man.)
In between working on Crashing and doing stand-up, Holmes hosts a weekly podcast called You Made It Weird, where he explores deep (and occasionally weird) thoughts with a performer or thinker. Apatow had once been a guest on the podcast, and that paved the way for Holmes to pitch him the idea of Crashing. Managing to be both indulgent and addictive, Holmes’s podcast interviews often cover terrain similar to his discussion with Penn Jillette. But most of these conversations stretch out for two hours, sometimes even three.
In contrast, each episode of Crashing is supposed be under 29 minutes and 30 seconds. Despite being drawn to the serious spirituality stuff, Apatow and Holmes work to make sure it never overwhelms the comedy.
The heavier scene with Jillette is sandwiched between two packed with laughs. It’s not bad enough that Pete is living in a garage in season 2. The garage belongs to the man he caught his wife sleeping with, a New Age spirit named Leif. When Leif tells Pete he needs to pay rent, Pete yells, “You [slept with] my wife!”
“Yes,” Leif replies as calmly as a yogi. “I [slept with] your wife. But that doesn’t help pay the bills. Believe me, I wish it did.”
Crashing is fascinating for how closely it tracks Holmes’s real-life story, from how he used to interact with his mother (less like her son and more like a wine-sipping, gossip-dishing best friend) to how his marriage collapsed amid drift and infidelity. More fascinating are the important ways his fictionalized version departs from the facts of his life.
* * * *
Pete’s parents, Irena and Jay, met at a singles bar on Cape Cod called the Hunt Club. When they wed, Irena, who is now 76, was 30 — late for her generation. “I wanted to get married,” she says, “but there wasn’t anyone who quite fit the bill.”
“And that bill was?” I ask.
She waits a beat. “Someone who wanted to marry me.”
Comedic timing runs in the family. Pete gets his cerebral humor and facility with wordplay from his mother, a former technical writer. His social intelligence and hammy ease with strangers come from his dad, a self-made businessman who delights in repartee with waitresses. (“No water for me. Fish make love in it.”)
Irena was clear-eyed in what she wanted most in a husband: a provider. Jay may have grown up in a working-class Irish and English family in Somerville, but by the time they met, he had the swagger of a man who was going places. (He would become successful in real estate and his oil tank removal business, hammily named Tanks-a-Lot.)
Irena was born in Lithuania during World War II, and from ages 2 to 7 she lived in a displaced persons camp in Germany. War and deprivation permanently scarred her parents. Even after they moved to South Boston in 1949, she says, they were forever petrified that more hardship would befall them. Their worry seeped into their daughter’s psyche. “I was anxious all the time.”
That’s why, when she had her own kids, she says, “it was just so very important to me to give them absolutely the best of everything.”
That, more than anything, explains why Pete and his brother, John, who is two years older, were raised as evangelical Christians. When Pete was in the second grade, the family moved to the desirable suburb of Lexington. “I wanted him to have classy friends,” Irena recalls, as I sit with her and Pete in the living room of the family’s new home overlooking a lake in Arlington. A chance encounter led her to Lexington’s Grace Chapel, one of the only evangelical megachurches in the region. There, Irena was thrilled to find lots of bright high-achievers — “my kind of people,” she calls them. If, she says, her aspirational pursuit of friends sounds snobby, it was all part of her determination to give her boys the sense of security she never had as a child.
Pete took to evangelicalism even more than the rest of his family, eventually leading a Bible study group and becoming part of the church’s “worship team.’’ He loved the vibe at Grace Chapel. “These people,” he says, “were bound by spiritual belief to be nice!” It was a sanctuary from the noise at home, where his parents often squabbled. Pete would play peacemaker, sometimes easing the tension by grabbing his keyboard and singing nonsensical songs he wrote. (“I am a cow giving birth!”)
He was close with his mom — they’d often confide in each other on long “mom walks” after school — but less so with his dad. Having zero interest in sports didn’t help. Still, when his parents bickered, he felt he could understand both of them better than they could understand each other, so he took on the role of family translator.
By ninth grade, though, he had his own problems to worry about. He struggled with the transition in 1993 from his nurturing Quaker grammar school in Cambridge to sprawling, competitive Lexington High School. His anxiety got so severe he developed a bald spot on the side of his head.
While his over-the-top cheeriness had played well at his private Quaker school and at summer camp, it fell flat in a public high school of 2,000 students where coolness was measured in sullen detachment. “I was participating, being nice to the teacher, never keeping my mouth shut,” Pete says. “I was big and goofy, and had a soft face and braces.” Even though he wasn’t gay, he endured plenty of gay slurs from the school’s jocks — called “the white hats” because of how they accessorized their Abercrombie & Fitch duds with white baseball caps.
He had two close friends, but rather than deal with the temptations of drinking, drugs, and sex, he spent most weekends alone in his room. He loved playing with action figures, crafting back stories and narrative arcs for them, having them die and then come back to life. When he was 18, his father told him, “I think you’re supposed to stop doing that” and sold his son’s action figures.
He accepted all the messages he was getting at church. “I bought it hard.” When he and some other boys asked a lay church leader if they could still be considered virgins even if they masturbated, he found the man’s answer less than reassuring. “Technically, yes.” But Pete didn’t push back. “I trusted grown-ups a lot.”
As much as his conservative Christian beliefs were out of step in progressive Lexington, they unexpectedly helped develop his comedic muscles. If classmates tried to buttonhole him on some of the more exclusionary tenets of his religion, he’d deflect with a joke. “I learned to use laughter as a lubricant,” he says.
He blossomed at Gordon College, an evangelical outpost 25 miles north of Boston with a smaller student body than his high school. He was comforted to find himself a really big (6 foot 6 inch) fish in a pretty small pond.
He came into his own in college as a performer, helping found an improv comedy troupe. It took hold on a campus where slipping in the word bastard felt as edgy as dropping an f-bomb in community theater. He found a mentor in his communications professor Mark Stevick, who was also a playwright, ran an off-campus theater troupe, and hosted a dinner-theater show. Not long after joining that troupe, Pete emerged as one of its star performers.
It was during a break in the dinner-theater action at a North Shore restaurant when Stevick first suggested Pete give stand-up comedy a try. When he demurred, Stevick jumped on stage to show him how easy it was. The professor pointed to a sign behind him for Mike’s Hard Lemonade and cracked, “What’s so hard about lemonade?” Pete laughed, maybe because he knew how simple it would be to improve on the joke.
Most important for Pete, Stevick’s theater troupe got him close to Becca, a fellow company member who was two years ahead of him at Gordon. They soon began dating.
Although Pete envisioned himself becoming a pastor someday, after graduating from Gordon in 2001, he decided to take a shot at comedy. He did five open-mike nights in the Boston area. He wasn’t very good, but it felt like something he could grow into. He decided to give improv comedy a more serious try by moving to Chicago, the land of Second City.
Before he made the move, he asked Becca to marry him.
* * * *
In last year’s pilot for Crashing, Pete comes home unexpectedly to find his wife naked in bed. As she composes an excuse, Leif emerges from the bathroom, naked except for a washcloth.
In real life, Holmes tells me, discovering his wife’s affair was both less dramatic and more heartbreaking. After living in Chicago, where he bonded with fellow struggling comics like Kumail Nanjiani, Kyle Kinane, and Hannibal Buress, Pete and Becca moved to New York so he could take his comedy to the next level. She got a job teaching at a school in Brooklyn and initially supported them both while Pete scrapped for stage time.
Occasionally Pete joined Becca and her teacher friends after work for drinks. He hit it off with one dynamic teacher and made a point of sitting with him at the bar during group get-togethers.
The last time he met up with them, though, the guy was visibly uncomfortable when Pete tried to talk to him.
Shortly after that, Becca sat Pete down and told him about the affair she was having with the teacher whose company Pete enjoyed so much. Suddenly, it made sense. “Everyone knew except me,” Pete says. “And he felt terrible. He didn’t want to fake it anymore.”
“This is why the show is such a good exercise in empathy,” Pete says. “I considered what it must have been like for him!”
The fact is, the guy liked Pete as much as Pete liked him. “It’s hard not to like me,” Pete says. “I wasn’t abrasive. I was a sweet kid. I just got married too young. And then my wife fell in love with him. At a job that she got so I could pursue my dream.”
One of the plot mainstays of Crashing — where Pete is playing his 28-year-old self — is that, even after his divorce, Pete’s ex-wife and her new partner remain in his life. In real life, though, Pete hasn’t spoken to either of them in a decade.
I ask him if Becca is still with the dynamic teacher. “I think so. Last I heard. They have no Web presence,” he says, sounding like a person who has searched Facebook for them more than once.
He says a mutual friend who still keeps up with Becca told him he saw her at a function last year, that she was married with a couple of kids, and she was doing well. “I was happy to hear it,” Pete says.
That mutual friend turns out to be Mark Stevick, their former Gordon professor and theater company leader. I grab coffee with him in a Salem cafe not far from where a despondent Pete met him right after the breakup in 2007. Stevick tells me that as fond as he’s always been of both Pete and Becca, he had harbored doubts about their life together. “I did worry when they got married that Pete’s ambition would overwhelm Becca,” he says. “They’re both bright lights.”
Of the Crashing character modeled after Becca, Stevick says: “It seems like that is Pete’s homage to how important Becca was in his journey. Pete has moved on and made art and flourished. But I keep wondering what it must be like for our friend Becca to see all this.”
Stevick says he’s never asked Becca what she thinks of the show or if she’s even seen it. Out of respect for her privacy, both he and Pete decline to reveal more than her first name.
I manage to find her on my own, though. Something Stevick had said stays in my head: “In a divorce you split up material things, but both people lay claim to their shared narrative.” In an e-mail, I ask Becca for her insights on the narrative she once shared with Pete.
Her reply is polite but firm: “I’m sorry to seem obstructive, but I . . . request total privacy for me and my family.”
Stevick tells me his last communication with Becca was a volley of texts in late October. She had reached out because that day’s weather reminded her of all the beautiful autumn days she had spent with his theater troupe in Salem. Stevick texted back to say he was actually in Los Angeles, for Pete’s wedding to his longtime girlfriend, Valerie Chaney.
As crushing as it was for Pete when Becca left him, he took one thing she said before departing as a beautiful gift. “You’re going to be one of the greats,” she told him, at a time when calling him a struggling stand-up would have been generous.
“That,” Pete says now, with a big smile, “almost made up for the affair.”
He delivers the line as a joke, but there’s clearly truth to it. The way he looks at the situation, Becca got what she wanted: marriage to a guy who shares her interests, like the outdoors. (Pete preferred playing Nintendo.) And he got what he wanted, not just a thriving career but also his marriage to Valerie, who works for a nonprofit devoted to improving self-esteem in girls. Valerie also loves the comedy world and has become his collaborator.
“Because an affair that I didn’t want or ask for set me free,” he says, “I really do see it as grace that my wife left me.”
* * * *
In a steamy morning in August, the season 2 finale for Crashing is being filmed inside the chilly Gotham Comedy Club in Manhattan’s Chelsea neighborhood. It’s a roast scene, guest-starring roast master Jeff Ross, who turns out to be much less mean-spirited than his take-your-lumps Rickles reputation. After a quick rewrite, Crashing’s producers hand Ross a line of dialogue slamming former America’s Got Talent host Nick Cannon (“That joke was so bad even Nick Cannon couldn’t fake a laugh for it”). The nasty roast master declines, protesting that Cannon “is a nice guy!” So costar Artie Lange delivers the line instead.
In between takes, talent manager Dave Rath tells me why he took Holmes on as a client. “Pete was so serious about his comedy work but was otherwise so innocent and doe-eyed about the world,” Rath says. Even though Holmes was making very little at the time, he rented an office with fellow comedian John Mulaney, where they would go, with Seinfeld-like discipline, to write every day. Like Mulaney, Holmes has always managed somehow to look younger and act older than he really is. Although he has no children, Holmes has joked for years about how he looks like a suburban dad at a barbecue.
Crashing recaptures a lot of Holmes’s innocence. “This show is as much about Pete’s spiritual journey as it is about his comedy journey,” Rath says. “I think Pete would tell you that he is basically an atheist now.”
It’s a common assumption. After all, Holmes has drifted far from the unquestioning devoutness of his pre-divorce self. And he’s done his drifting in full public view, engaging in behavior he once considered sinful, egged on by so many nonbelieving comedian friends. But the assumption turns out to be wrong.
When I ask Holmes how he would describe his faith now, he says, “a Christ-leaning spiritual seeker.” He doesn’t go to church anymore, but says he no longer feels he needs a building to practice his faith. “To me, the game is to never not be in church.” After hewing to the rules of his religion for so long, he says what he now most wants in a faith is something that makes him feel freer, rather than more constricted.
He actively and aggressively explores various faith traditions, looking for inspiration and nourishment. At times, he can seem so eager for enlightenment that he steps right over it.
Judd Apatow says that when he listened to Holmes’s podcast with Apatow’s mentor, Garry Shandling, just a few months before the legendary comedian’s death in 2016, he grew frustrated. “Garry started a sentence where he was about to tell Pete about this experience that changed his life, and Pete changes the subject!” Apatow says. “It really is one of those moments where someone is about to tell you the meaning of life.”
Still, other portions of the interview make it essential listening. Although Shandling, unlike Holmes, never wove spirituality into his comedy, he was even more of a searcher and farther along in his journey.
Holmes sometimes seems as if he has replaced his reliance on the strict teachings of conservative Christianity with a reliance on the be-here-now, love-everyone Eastern teachings of guru Ram Dass. Born 86 years ago into a Jewish family in Newton, Richard Alpert stepped off the path of a successful Harvard professor, tuning in and dropping out with psychedelic Harvard colleague Timothy Leary, before heading to India for enlightenment and rebranding as Ram Dass.
How often does Holmes quote the guy? Let’s just say that if we were playing a drinking game, and I had to take a swig every time he said “Ram Dass,” I would quickly find myself in no position to drive home.
When I mention to Holmes that Shandling seemed to be cautioning him against leaning too heavily on Ram Dass or any other guru, he concedes the point. “To answer a suggestion that I quote Ram Dass too much,” Holmes tells me, “I’ll quote Ram Dass! He says all methods are traps, but in order for the method to work, it has to trap. That’s where I’m at.” Shandling, he says, had evidently already transcended the trap.
In fairness, Holmes has more than just one spiritual guide. Another of his favorites is Rob Bell. The evangelical pastor founded a megachurch in Michigan but lost support from many conservative Christians when he espoused a more forgiving, open-armed faith in his best-selling book Love Wins. Bell said he was inspired to write the book after one of his congregants insisted to him that Mahatma Gandhi was burning in hell because he hadn’t been a Christian.
“That book changed my life,” Holmes says. As someone who grew up obsessed with avoiding any behavior that might land him in hell, he is still curious about the afterlife. But his primary focus is on the here and now.
I ask Holmes if he still prays. “Now I look at prayer as a way of accepting what is,” he says, “rather than a way of hacking into the code to change what is.”
Yet he sometimes still uses prayer for more than just acceptance. When he was waiting to hear if HBO would commit to Crashing, he says, “I called Rob [Bell] and just straight up said, ‘Will you please pray that my pilot gets picked up?’ ”
During my interview with Holmes and Chaney at his parents’ house, the conversation returns often to faith. Chaney is the daughter of two Christian pastors, though she considers herself a searcher like her new husband. Bell officiated at their wedding.
Holmes mentions that he sent a copy of Love Wins to his mother, with some trepidation. “You loved it!” he reminds her. “You called me on my birthday to tell me that. That was the best birthday present I’ve ever gotten.”
Irena Holmes remains an avid churchgoer. I ask how her son’s spiritual journey has affected her.
“He shakes my faith, regularly!”
She follows the line with such a big laugh that I can’t tell how serious she is.
“In what way does it shake your faith?”
Her smile fades. “I start thinking of it in different ways,” she says. “Unfortunately, he’s smart, so it makes me think.”
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Crashing has introduced an interesting dilemma for Irena. She is her son’s biggest superfan, but there is a notable exception to her parental beaming. She hasn’t mentioned the HBO show to any of her friends at Grace Chapel. She first jokingly suggests that’s because the actress who plays Pete’s mother on the show looks nothing like her. “What can you do?” she says. “Annette Bening was not available.” (Irena looks a lot like an older Bening, especially when she squint-laughs.)
The real reason she doesn’t bring up the show with her church friends has nothing to do with casting. She says that because of the raunchy content, “I know no one’s going to like it.”
* * * *
“Pete’s a guy you root for,” Artie Lange tells me, in his trailer during a break in shooting.
A lot of people also root for Lange in the face of his messy, ongoing struggle with heroin addiction. The former Howard Stern sidekick says that although he’d never met Holmes before joining the Crashing cast, the trust they’ve developed made him willing to weave his real-life pain into the show’s story line. “Everyone has a struggle,” Lange says. “Pete’s struggle is coming to terms with how everything he believed, and he built his life around, is not true.”
In the end, Crashing is mostly about growth. In season 2, viewers will see Pete develop into a much stronger comedian. They’ll also see him progress from denial over his breakup, which dominated season 1, to acceptance. He’ll begin a season-long relationship with “Ali,” a more jaded fellow comedian. The role is played by comedy writer Jamie Lee, a friend who worked with him on his short-lived TBS talk program, The Pete Holmes Show.
As it happens, Holmes and Lee dated in real life for a year, though unlike in the show, she wasn’t his first girlfriend after his divorce. Four weeks after his wife left him, Holmes began a relationship that lasted a year. A few weeks after that breakup, he began dating Lee, and a few weeks after Lee and he split, he began another yearlong relationship. “I was so codependent,” he says. Prior to meeting Chaney, he had remained single for a year and a half, an experience that taught him independence.
He learned other things about himself after his divorce. As close as he is with his mother, he found that, in his heartbreak, he needed less of her there-there comfort and more of his father’s suck-it-up grit. He spent more time with his dad and his older brother, drawing them all closer. Surprisingly, it was seeing how much his divorce crushed his father that led to their stronger bond. Hearing his tough father’s voice crack over the phone, he says, “is the only memory I have of being really mad at my ex — that this tiny, physically speaking, woman had taken down this metaphorically giant man.”
There are limits to this personal growth, though. Last year, when he shared the news that he would be opening for Dave Chappelle at Radio City Music Hall, his dad’s only response was “Carnegie Hall or bust!”
Holmes says he figures his father is only trying to keep his son grounded. Those doses of withholding increase Pete’s drive. He finds fuel in lots of places, like his teenage memory of playing Super Nintendo at the Burlington Mall. A chunky kid waiting for his turn at the controls pointed to the moles on Holmes’s face and said, “Why don’t you go get some Clearasil to clear those things up?”
The kid probably never thought about that slight again. But to this day, when something great happens in Holmes’s life, like Crashing getting picked up, he says, “I think of that kid.”
Pain like that never fully fades, it simply becomes more manageable, he says. “You are just trying to heal yourself in some way.”
The desire to help others once made him want to become a pastor. Yet in publicly exploring his private pain, he’s been surprised to see how many souls find healing through his journey. To the most devout evangelicals he once prayed with, the profane, taboo-busting Pete Holmes of today probably seems unrecognizable. But that doesn’t mean he hasn’t found his ministry just the same.