Comedian Pete Holmes is an enormity, towering at 6 feet 6 inches tall. When performing one of his stand-up routines, that height is exacerbated by an elevated stage and seated audience. And yet, he is anything but intimidating. His gleeful, chipper jokes are always doled out with an ear-to-ear grin. When listening to his podcast, “You Made It Weird,” one often has to adjust the volume to account for his booming, goofy laugh.
In an interview with The Daily Free Press, Holmes discussed his accomplished career in comedy. The Lexington native boasts a resume that includes three stand-up specials, two comedy albums and a semi-autobiographical television series, “Crashing,” which was renewed for a second season on March 15.
Holmes’ mother and father — of South Boston and Somerville, respectively — might have something to do with it. The 38-year-old credited his success to his upbringing, saying that both of his parents “are very funny people.” Considering the large number of fellow comedians from the Greater Boston area, he noted their strong work ethic, adding with a laugh that “living through those winters may have something to do with having a good sense of humor.”
His Boston roots get something of a tribute in “Crashing” in the form of the Boston Comedy Club. When he was just setting foot on the New York comedy scene, Holmes said it was fellow Bostonian and comedian Bill Burr who recommended the West Village venue as a place to begin “barking,” or handing out flyers in exchange for stage time later in the evening. Recreating the interior of the club for “Crashing” offered a surreal flashback to Holmes’ days as a struggling comedian a decade earlier, he said.
Remembering that time, Holmes said he would “try and take comfort in the fact that I knew that so many other great comedians had done that exact same thing.” For him, standing on a New York street corner in January was simply a required step toward becoming a successful comedian.
“It becomes a rite of passage as opposed to just unnecessary suffering,” he added.
“Crashing,” which is loosely based on Holmes’ life, involved quite a bit of rehashing old memories, not all of them as fondly recalled as those of barking and 3 a.m. performances. At the time, Holmes was undergoing a divorce after he was cheated on by his wife of eight years. Revisiting those memories was anything but easy. He noted that to relive those difficult moments repeatedly while working on “Crashing,” was “trippy … It was almost like The Twilight Zone.”
But, this time around, he has some support. He proposed to his girlfriend, Valerie Chaney, on Feb. 9, and noted how essential she has been to the creative process on “Crashing.”
“As I’m making a show … inspired by my divorce, it’s really nice to have the circle … spill out on the other end and find the right person to marry,” he said.
He added that Chaney provides a much-needed steadiness to reflect upon unstable times.
“Such a huge part of life is to be able to retell some traumatic event with a smile and look back and actually be grateful for them,” he said.
This graciousness translates well in Holmes’ brand of comedy, which is centered around positivity. He frequently refers to “uncircumstantial happiness” in his podcast, and joy is a persistent theme throughout his work.
Adam DeAngelo, a junior in Boston University’s College of Communication, is a fan of Holmes’ podcast, noting that it was his favorite of Holmes’ work because it is “just his personality.”
His personality, while multifaceted, is driven by honesty, a near-constant state of merriment, and kindness not often seen in high-profile celebrities.
His friendly, easygoing nature is part of a glowing charisma that allows Holmes to connect with audiences and fellow comedians alike, including longtime friend and two-time podcast guest John Mulaney. In an email correspondence, Mulaney reminisced about the moment when they first met in 2005 and discussed a couple of his jokes. “I don’t recall a moment after that when we weren’t friends,” Mulaney noted, adding that over the course of two years of Sunday breakfasts, they “almost exclusively discussed what it meant to be a man and a good person.”
Being a good person and bringing happiness to audiences is what distinguishes Holmes in a cynical industry. Mulaney, like many of Holmes’ fans, takes pleasure in Pete’s gleeful style, noting that “he wants his audience to feel joy and sometimes tries to strong-arm them into it. It’s a delight.”
At its core, that delight stems from the joy of doing what one loves.
“I know that the truest part of 20-year-old Pete would have been purely excited, just thrilled,” Holmes said. “You can find holiness and goodness and light in some of the most unexpected places.”