Finding the funny in every day life

Saturday, 8 February 2025

Josh Wolf was a struggling single dad with three kids living in a one-bedroom apartment in Los Angeles when he set up a peanut butter and jelly sandwich delivery service to pay his bills. Now an acclaimed US stand-up comedian, writer and podcaster, the 54-year-old had a tough road to get to where he is today.

He was in his 20s and his marriage ended when he moved his young family from Seattle to Los Angeles to try to get ahead in the stand-up comedy scene. But gigs were rare and poorly paid. Tickets to his shows were often given away, and he had a good few years when no-one knew who he was.

He couldn’t afford childcare as he took the odd comedy gig, so he and the kids would make sandwiches and put them in brown paper bags, with a scripted note from Wolf pretending the lunch was from “Mom’’.

The last menu from his peanut butter delivery service – which was eventually shut down when a health inspector found them making the sandwiches in their apartment - is one of the sentimental items tacked on a wall behind him in his Las Vegas studio: mementoes from his life and his career.

It’s hard to believe now that the warm, affable, funny guy whose comedy clips have amassed more than 20 million views was once wondering if he’d chosen the wrong career. But his funny tales of being a single dad struck a chord, and he was picked up by 20th Century Fox, and began performing on E!'s late-night talk show Chelsea Lately.

Now known as one of the best storytellers in the comedy world, he’s giving Zoom interviews ahead of a tour to Australasia. He cracks jokes from Jimmy Kimmel’s Comedy Club in Las Vegas, where he has a weekly residency. Dressed in a pink sweatshirt and a signature black baseball cap, Wolf waxes lyrical about New Zealand, which he last visited in 2023 for sold-out shows. Wellington is a vibrant city and he can’t wait to return, apart from the bumpy landing into it, he laughs.

Behind him, there are photos of his family, including his three children who became the butt of his jokes in his stand-up. Listen to his Father of the Year’ series on Spotify if you haven’t already, where he shares tales.

Wolf has nailed the funny single dad space, and his imitation of teenage boys is also spot on, according to my friends with sons who have listened to his comedy clips. Rolling his eyes, he says: “They’re the dumbest demographic in the world. The boy from age of 14 to probably 25 is so dumb. And they know it.’’

Growing up in Massachusetts he was that dumb teenage boy, with three brothers who were all the same. “Doesn’t matter how smart you end up, you’re pretty dumb for about eight years.’’

He imitates the teenage boy laugh, which is hard to turn into script. You’ve got to listen to it to get it, but he’s been mimicking it for 25 years.

More recently, he’s been making people laugh on live shows about dating, messing with his wife of two decades – screenwriter and director Beth Wolf - and man boobs. “Never seen a c-cup look so good on a man,’’ he sings in Man Boobs’, on his 2022 comedy series, Here for the Fun.

On this tour, High on Life, his biggest tour to New Zealand yet, he’s performing with his son, Jacob, who featured in many of Wolf’s funny jokes and fell into comedy by chance.

Jacob, now 27, used to accompany his father to the events to sell merch, until Wolf pulled him up on stage one day for a Q and A. “We went out there and the chemistry was amazing and Jacob caught the bug, because that live laughter is so addictive.’’

The pair now have a weekly podcast, Hey Maaan: A Father & Son Comedy Podcast, where they have a laugh about pop culture, current events and the generational divide: recent episodes are on the LA fires and, late last year, Jacob talked about his struggle with addiction and his sobriety journey.

Wolf has learned more about his son from the podcast. “I do it because I hang out with my son for 1½ hours a week. He has no choice but to talk to me and answer questions.’’

In his stand-up, Wolf doesn’t crack jokes about politics, or social issues, or anything too heavy. Instead, his show is fun and entertainment, an escape from worrying about the mortgage or whether you’re going to lose your job.

If anyone is offended by some of his outrageous stories and anecdotes, that’s their problem.

In this tour, he’ll be sharing stories which are relatable and funny. “When I get off stage, people feel like they’re hearing their friend telling stories in the backyard.’’

“I keep trying to tell my kids that we grew up differently. No kid can understand that we were raised unsupervised. Everyone over the age of 40 thinks of 10 times when they should be dead … I talk a lot about different generational things, but always super relatable.’’

He won’t be talking about Trump’s tariffs, or talking about politics. “My job is for you to come to my show and stuff goes away.’’

We talk about empty nesting. It’s been years since his kids lived at home, and people are often surprised that his older two are now aged 31 and 32, partly because many of his funniest stories are about raising them when they were young. But some of the stories won’t be revealed – or they’ll be slightly tweaked – until one is happy for it to be shared, often years later. “It’s not my job to make fun of my kids on the internet.’’

Being on Chelsea Handler’s show from 2010 to 2015 propelled his career and touring with her was fun, including performing live at New York City’s Radio Hall. “My parents were there and for the first time, they said: ‘Oh okay, you’re doing something now’.’’

He’s also hosted TV shows, written a book about being a single dad, acted in sitcoms, and another highlight was his own late-night TV show, the Josh Wolf Show.

In his mid-50s, the charming, warm Wolf is having the most fun he’s ever had, touring, podcasting and performing with his son. His style of humour isn’t unique, and while he was warned New Zealand audiences might not respond like Americans, we absolutely do.

“They've been very high energy, polite but great crowds and I'm telling you if you want to come and have fun for an hour and just forget and laugh, I'm your guy.’’

• Josh Wolf is performing at Wellington’s Hannah Playhouse on February 14 and Christchurch’s The Piano on February 15. For tickets and tour details: eventsinnovated.com