
Pete Holmes has a new special out. Spoiler alert: It’s good. Not my favourite, which is probably “Dirty Clean” from 2018, but it’s up there, and if I revisit it a year from now it might get an upgrade.
I’ve been meaning to discuss Pete Holmes for a long time now, because his approach and disposition is so very different from other comedians.
It’s something he’s parodied himself. He has a spot-on impression of a bitter and condescending angry comedian being outraged and snarky that there’s a new flavour of biscuit. Cynical and pissed-off seems to be the default position of many comics, especially the “I identify as a helicopter. My pronouns are fuck/you” kind of conservatives.
Doing comedy from a position of happiness and optimism sounds childish, but there’s a big difference between childish and child-like. Holmes’ first album was titled “Impregnated with Wonder,” and it feels appropriate for a comedian who operates from joy. Shared annoyance is not the only way to connect with people. An expressed sense of glee and amazement also invokes that same sense of communion and shared experience that is so much of what stand-up comedy aims for.
This always gets me with Holmes’ comedy – it’s fun. Fun in a way that most stand-up seems to have forgotten. This is something that he credits Gary Gulman with. If you’ve read my book or follow my ramblings here you’d know that I consider Gary Gulman to be the absolute G.O.A.T of stand-up, especially of writing it, so when Gulman was a guest on Holmes’ “You Made It Weird” podcast I tuned in.
That they’re friends and contemporaries should surprise no-one, as they both came up in the Boston comedy scene that Dane Cook, Bill Burr, Patrice O’Neal, Mike Birbiglia, Greg Giraldo, Louis C.K, Steven Wright, Doug Stanhope and many more.
I was still stunned, though, when Holmes told Gulman that seeing him perform changed and validated his own approach to comedy. Holmes looked around at all the bitter misanthropic comics and thought “that’s not me, I can’t summon that kind of energy, I don’t think I can do that.” Until he saw Gary Gulman’s act, which proves that you don’t have to be bitter to be funny. You can be playful and clever without putting all of your jokes through a resentment filter.
I’m not sure if I’m especially joyous, silly or playful in my own act, which is surprising since I love the comics who are (Pete Holmes, Gary Gulman, Kyle Kinane) but I think it’s important that all comedians, regardless of their style, make themselves aware that there’s ways to bring a roomful of strangers together and laugh without cliched venom.
Pete Holmes has an excellent body of work. His TV show, Crashing, is one of the best and funniest shows about stand up comedy. His book Comedy Sex God is a highly recommended autobiography with some amazing insights about religion and spirituality as well as the path of the comic. He’s done some excellent specials and his podcast is one of the few I consider to be worth my time.
But for now, I recommend you check out “Silly Silly Fun Boy” on YouTube. I’ll embed it below but you will probably have an easier time with this link. It’s not just a good special, but an exercise in positive, joyful stand-up.

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