‘Crashing’ Season 2 Arrives on HBO With Pete Holmes and New Lead Jamie Lee

Aaron Berke

HBO’s hit comedy series “Crashing” premieres its second season this Sunday, telling the next chapter in stand-up comic Pete Holmes’ journey from couches to comedy clubs. Partially based around Holmes’ real-life experiences as a struggling comic in New York City, the first season saw Pete unceremoniously jettisoned from his comfy suburban life after he found his wife cheating on him. As Pete took the opportunity to begin pursuing his comedy career in earnest, he found himself crashing on the couches of real-life comedians like Artie Lange, T.J. Miller, and Sarah Silverman, who all appeared on the show as themselves. This begun the series’ unique format of paralleling Pete’s personal life with his journey from couch to couch. Every time Pete crashes, he gets an opportunity to bounce back.

Season 2 features a continuation of this format, but with a Pete much more willing to dispense with his good Christian upbringing, and fully embrace the wild and chaotic life of a New York City comedian. The season takes Pete through a variety of whacky scenarios, including his first ever drunken hook-up with another comic, a three-day adventure with comedian Bill Burr that turns into a social media nightmare, and a journey through New York that ends with Pete’s wedding ring blown to smithereens by a bomb squad.

“This season is really wild. This season is covered in sin already,” laughs comedian Rachel Feinstein, who appears in both seasons of “Crashing” as herself, “Pete definitely goes rogue this season.” Writer/actress Jamie Lee, who plays Pete’s new love interest, Allie, agrees, “He does [go rogue]. It’s Pete unleashed.”

Lee, Feinstein, and actor Zach Cherry recently sat down with Entertainment Voice to chat about the new season of “Crashing.” Lee, who juggles writing and acting duties on the series, commented on Pete Holmes’ openness, and the joys of mining founts of material from his past. “I feel like he’s been very open book about wanting to mine his own experiences,” said Lee. “We start with the nugget of truth and then figure out a way to work it into the narrative. It makes writing super easy because you’re not dealing with someone who’s closed off. He’s just like, what do you want to know?”

In season 2 of “Crashing,” Pete has on-again off-again relationship with Lee’s character, Allie. In the season 2 premiere, “The Atheist,” they meet initially at the Boston Comedy Club, where Pete watches Allie’s stand-up routine. Later, they encounter each other at the bar after Pete’s wild club night. Pete and Allie engage in a totally unexpected night of passion, but their hook-up has some unintended consequences for Pete, who, due to his rigid upbringing, doesn’t quite understand the concept of casual sex. The experience is a first for the formerly devout Christian, but it’s all part of Pete’s emotional growth. Pete ultimately runs into Allie again in a later episode. A considerably looser Pete helps Allie with her various NYC comedy club appearances as they flirt and riff off each other as only two comedians can.

Pete and Allie’s relationship is refreshing and funny, bringing a lot of heart to the events of season 2. In many ways, Allie is the complete opposite of Jessica, Pete’s wife in the first season. Allie is funny, driven and open, a mixture that is the perfect antidote to Pete’s more inhibited qualities. “We took elements from a bunch of different things and sort of piled them into Allie,” said Lee. “[She] literally is all these different archetypes shoved into one character.”

Although Lee was already in the writer’s room on “Crashing,” she stated that being a writer on the show did not actually help her nab the role of Allie, “I think when you’re in a writer’s room you’re kind of the last person anyone thinks of, which is kind of weird because you’re right there,” said Lee. “You think ‘well I’m here, choose me.’ That’s not how it works… They’re gonna see everybody. You’re never going to circumvent the casting process.”

Still, Lee admits that she was able to mine her own experience as a stand-up comic for the role of Allie, who takes the viewer through New York City’s “alternative” comedy scene in the season 2 episode “Too good.” The episode depicts Allie’s unbridled determination to make it in comedy. Indeed, Allie goes so far as to perform in 4 or 5 clubs a night. Some of Lee’s own material is featured in the stand-up sequences. “A lot of my older stand up is in the show because we try to capture that slice of life from when you’re first starting out, and those were the jokes I was telling back then,” Lee said. “I think the fact that I went through pursuing standup in New York, I think that was the most valuable tool. Just to be like ‘oh I went through this.’ So it’s kind of cathartic to depict it on TV.”

Meanwhile, Zach Cherry, who is one of the few actors on “Crashing” without a stand-up comedy background, still manages to bring his own unique experiences into the role of Chicken Wing Man, which includes a lot of improvisation. “I bring none of my material. I do bring my technique and having a beard,” Cherry said with a laugh, “My wing eating technique [is there]. There’s a little bit of my personality in my character.”

In season 1, Pete shared a number of funny scenes with the Chicken Wing Man, which mostly involved Pete asking for stage time and Wing Man casually shooting him down (while eating chicken). Season 2 upends this formula with a hilarious scene in which Wing Man approaches Pete at his new part-time ice cream shop job, offering to be Pete’s manager. Pete, of course, is ecstatic. It turns out, though, that Wing Man thought Pete was a completely different comedian. Luckily, Pete’s new job winds up being the ultimate arbiter, as Wing Man agrees to be Pete’s manager in exchange for a free ice cream.

Holmes and Cherry share a wonderful chemistry in their scenes together. Cherry, who seamlessly blends in despite his lack of a stand-up comedy background, noted that, as an outsider to the world of stand-up comedy, “Crashing” has taught him a lot about the actual rules of stand-up. “Since I don’t do standup, I learn all this stuff from watching ‘Crashing,’” said Cherry thoughtfully. “I didn’t fully know what that [world] was.’”

One of the most distinctive elements of “Crashing” is its ability to seamlessly blend hilarious staged segments into the actual reality of stand-up comedy in New York City, a theme which continues throughout season 2. One prime example is during the episode, “Porter Got HBO,” when Pete’s friend, Porter, winds up having a panic attack before his first appearance on live television. Pete tries to calm Porter down as he neurotically shaves off his entire beard. A distraught Porter fears mockery, but he sucks it up, gets on stage, and performs anyway. The sequence is both hilarious and authentic. The authenticity of “Crashing” sets it apart from other television shows about comedy, managing to find that sweet spot between reality and entertainment.  

“It’s really fun,” said Feinstein on the nature of filming for “Crashing,” which generally allows the actors to replicate their real stand-up comedy experiences. “[If let’s say] I have a spot in a few hours at the [NYC Village] Underground, [during the shoot] you’re gonna sit here [at the Underground] and eat some wings and mock the same people you would be mocking anyway… It’s nice to actually see what really happened on a show, that it’s documented and not made to be shinier.”

Lee agrees, citing the need to meld comedy with accuracy, “I think with “Crashing,” part of the promise of what we’re delivering is the accuracy as well [as the comedy] because it’s technically something that very few people know about outside of our bubble… We speak a different language. [The world of comedy] is so insular.”

Cherry compared the experience of a comic watching “Crashing” to an improv artist like himself watching the film “Don’t Think Twice.” “[It’s] an improv movie and I came up through improv,” said Cherry. “It’s not 100% accurate in my experience, but it is cool seeing it depicted because most people don’t get to see that. So for me [the accuracy] is almost more important [than the comedy]. It’s fun watching what you went through be depicted for a broader audience.”

Ultimately, Feinstein noted that with “Crashing,” there’s no real need to compare comedy with accuracy. It offers both in spades. “I don’t think you have to worry about the funny part,” Feinstein quipped. “You have all these hysterical comics and [the series] is written by really funny comics. It’s already gonna be really funny, so you don’t really have to choose.”

In “Crashing” season 2, every time Pete gets a new comedy opportunity, an obstacle is hurled into his path. Pete gets to do audience warm-up for Dr. Oz, only to be dismissed after one day. Pete’s friend Porter gets an offer to do an HBO special, while Pete himself lingers in the background and watches. For every new opportunity, there’s also a reminder that the reality of New York stand-up is harsh and bitter. But all good things come to those who wait. “Crashing” season 2 features a moving thematic narrative, which suggests that long, hard struggles are a part of any career. Finding your path takes time, and that’s okay.

According to Lee, that dynamic is very much intentional, “We don’t want Pete [the character] to have too much success too fast,” Lee said of the show’s future, “So I think that gives us a really fun timeline to play with, because there really are a lot more milestones to be had before he makes it big, as they say in the biz.”

Chiming in on his own character’s future, Cherry addressed the Chicken Wing Man’s go-to topic: His love of food. “I eat chicken wings in season 1, and ice cream in season 2. I’d like to just eat a third thing in season 3,” Cherry laughed, “One new dish per season. Sushi, I don’t know.”

“Oh wow,” laughed Lee at the mention of sushi, “That’s more like season 6.”

We’re only at season 2, but somehow the idea of a season 6 doesn’t seem so farfetched. After all, it can take years to become a successful comedian. That’s just accuracy.

“Crashing” Season 2 premieres Jan. 14 at 10:30 p.m. ET and airs Sundays on HBO.