On HBO’s Crashing, former Chicago comedian Pete Holmes plays a green stand-up named Pete Holmes (role of a lifetime) who struggles to find his footing after his wife cheats on him. Their divorce leaves Holmes homeless and he resorts to couch surfing. Through a variety of humiliating misadventures he ends up in the company of more established comics such as Sarah Silverman, Artie Lange, and T.J. Miller. They pity Holmes enough to allow him to spend the night, but the naive comic also gives them an opportunity to pump up their own egos by sharing their stand-up wisdom. Unshackled, Holmes gigs nightly and begins questioning his strict Protestant upbringing. The show’s second season, which began January 14, opens with Holmes, despite his lingering Christian guilt, enjoying a veritable bacchanalia of booze and women at a nightclub called the Hole with some new comedy buddies.

That’s what life feels like to me: really high highs and really low lows. One of the things the show is about is finding humor and a way to enjoy the low times as well as the high times. When you’re trying to become a comedian, there are so many low points, especially when you’re trying to redefine your life at the same time. I have a lot of people who have just seen the promos and stuff that are like, “I [also] accidentally said ‘I love you’ on a first date.’ ” People are relating really hard to that level of vulnerability, and I like putting stuff like that under the spotlight. I think a lot of times, especially in American comedy, we tend to shine the light on winning and killing it and success. I’ve always enjoyed shows that dip into more complicated space from time to time. I think people can relate, even if they’re not a comedian, to someone newly single trying to find his way. Whatever you’re going through can be projected onto that empty vessel.

—Pete Holmes

Looking at the list of performers from the Lyons Den, you get the impression the comedy scene was very dude-centric. Recently, a local comic named Meredith Kachel used statistics to empirically demonstrate men get far more bookings here. What are your thoughts on the barriers to entry for women in the comedy world?

You just named every talk show host minus one or two notable exceptions, like Jimmy Fallon.

It’s not so much that it’s a strange time to be a stand-up comedian or an actor or a producer or somebody in the public eye as much as it’s an unsafe time to be a woman. That’s something I’ve been meditating on. Maybe I’m an optimist, but my hope is that all of these stories coming out won’t just be a flash in the pan but will lead to real change in the way we treat each other. A lot of people point out, “Well, men feel unsafe [now].” Well, that’s how women have always felt. Now there really is a system of accountability moving past the shock of “Who did we catch?”