Harland Williams Bet on Himself and Won

My guy Harland Williams continues to be in my top five favorite comics. His brain works unlike any other, and I could listen to him talk for hours. So when I heard he wrote, directed, and starred in his own independent film, I was not surprised. I was just excited.

Wingman is a classic independent comedy. It reads like an indie film, but the comedy is absolutely competitive with box office releases. For anyone who feels like comedies are not getting made anymore, this will prove you wrong. The fact that it landed on both Apple TV and Prime Video is impressive for an independent project. If Harland can do it, so many others can too. This feels like the start of something, more comics backing themselves to create film and TV without waiting around for a distribution deal. That is the definition of betting on yourself.

Wingman follows a guy whose entire job is helping other men get laid, but underneath that premise is a deeper conflict about what the word "wingman" actually means and what real connection looks like. The movie could have had a box office feel, but there were choices made that go against that grain. Because Harland was the writer, editor, and director, I think it was genuinely difficult for him to decide what to cut. I usually do not feel like there is anything missing from a movie, but that was not the case here. Certain scenes felt forced, like they existed just to get more use out of a specific set. The car scenes were hilarious, but the most obviously low-budget. You could tell. It feels like some creative decisions had to be compromised for money reasons, which would not be the case in a big-budget production. That is not a criticism so much as an observation about what independent filmmaking actually looks like up close.

What worked in Harland's favor was the cast. Largely no-names who fit their roles really well. Russell Peters as Kazzim is the second lead and holds his own. Jamie Kennedy shows up and is great, but I wanted more of him. For a movie without people I already knew, I found myself rooting for the characters quickly. It often felt like this could have been two or three movies in one; there was that much going on. But it was inspirational. It made me feel like anyone with a vision and enough drive can make something real.

What a lot of young people may not realize is how long Harland has been doing this. His film debut was the pee-drinking cop in Dumb and Dumber in 1994. He played the hitchhiking serial killer in There's Something About Mary, Kenny the stoner in Half Baked, and the lead in RocketMan. My guy has range, and anyone who listens to one episode of his podcast knows this is how he is all the time. Always on. I am forever intrigued.

I am seeing him in a few days at The Carlson, and it will no doubt be a packed, exhilarating show. I am so grateful to get to experience my guy's chaos firsthand.