The Art of the Wingman: Harland Williams and Justin Levine Bring Back Comedy

In an era where broad, unapologetic comedy is making a comeback, the newly released comedy Wingman positions itself as a throwback with a modern edge. Directed by and starring Harland Williams and produced by Justin L. Levine the film blends chaotic slapstick comedy with a surprisingly grounded story about relationships and redemption.

Featuring a cast of comedy veterans including Williams, Jamie Kennedy and Russell Peters combined with Kayla Wallace (Landman) Evan Marsh (Shazam) Shiva Negar (American Assassin) and David Lipper (Full House) the film combines raw comedy and Hollywood talent. Lipper, Robert J. Daly and James Pratt (Malibu Crush) make up the rest of the producing team with Carly Granovsky serving as casting director.

Developed over more than a decade and rooted in Levine’s early concept -originally inspired by classic ’80s and ’90s dating comedies, Wingman follows a desperate romantic played by Evan Marsh, who hires an unconventional “Wingman to get his girl back triggering a series of increasingly outrageous misadventures.

Currently in selected cinemas and streaming on Apple TV+ and Amazon, we sat down with Harland and Justin to discuss the funniest film of 2026 Wingman.

Q&A with Harland Williams & Justin L. Levine

Q: Was there a moment in the film where you surprised yourselves—either a joke that went further than expected or a scene that became more grounded or emotional than planned?

J: Yes we knew we had funny scenes from the very first day outside at the racetrack. Russell was ad-libbing lines with Evan Marsh – the extra’s were all laughing along with the crew – so from that moment on pretty much everyone involved knew the rest of the filming would be funny – Harland & Jamie did a lot of improv scenes to which all worked as they are seasoned comics

H: Yes, much of the physical humor went better than planned, things that came out of nowhere in the moment. Throwing chicken wings at people’s heads, stuffing dill pickles in mouths, using the body to sell a joke, funny walks and funny faces. Some of the improvised lines gave longer length to jokes and added new jokes that weren’t on the page. The use of perfume boxes to build emotional walls in the perfume store scene was really an on the spot cool moment. The scene on the balcony with Bob and the Wall Street girl became a great emotional beat, as did the bar scene with Bob and Holly when they kissed for the first time.

Q: A lot of the cast are people you’ve known for years—when you were writing, were there specific actors you had in mind for certain roles?

J : yes, I’ve known & been friends with Jamie & Harland each for over 17 yrs – in fact we did comedy DVDs together back in the day – Harland William’s Child Wild and Jamie Kennedy’s Heckler – I’ve met Russell many many years ago in Toronto & I’ve also known my EP David Lipper for over 25 yrs and also our lead Shiva for over 20 years too – its always more fun to work with friends

H: The Wingman role I originally wrote for my actor buddy Michael Rosenbaum, (Lex Luthor from Smallville, Sorority Boys) but he ended up not wanting to do it, so I stepped in to play the part. The other actor I had in mind from the start was Russell Peters. I knew he would be perfect for the part of Kazzim, and he was, he absolutely nailed it, and such amazing improv lines too. Jamie Kennedy was great as Eddie, bringing the perfect energy and antagonistic vibe to the character. For the rest of the cast I wanted to use great actors we auditioned. We got so lucky, all of them exceeded my expectations!

Q: Every project has a turning point where it finally feels real—was there a specific day or scene where Wingman clicked into place for you?

J: yes for me it actually really felt this way only the day before we started as I had my flight booked to go to set in my Stardust studios new building that Wingman was going to be filmed then knowing my 15 years dream for Harland & I to make this movie finally came true – I was also super happy to have my old friend Jamie Kennedy join our cast

H: Honestly, the morning we got on set is when it finally felt real. The night before shooting I had bought a plane ticket home because it looked like the whole thing was going to fall apart before the sun came up. Thankfully the stars aligned, and it wasn’t until that first morning on set that I finally felt safe that we were doing the movie.

Q: Beneath the comedy, the film is really about someone struggling with connection—how important was it to ground the comedy in something recognisable?

J: I’m all about old school slap stick comedies, we wanted to bring this back to moviemaking because it seemed like Hollywood just forgot how funny they were, how successful they became & how many stars were made from pure, crazy comedies

H: It’s deeper than that; it’s about conclusion, redemption, loyalty, and never giving up, on love or on who you are as a person. Beyond the crazy comedy it was important to me that the movie had a soul grounded in the emotions, triumphs and fears that face all of us. I wanted Turk’s role as a Wingman to have a greater purpose. He isn’t about being sleazy, at the end of the day it’s about preserving his own integrity. Something all of us strive for within ourselves. You have to watch the movie to understand this.

Q: Was there a joke or sequence you fought to keep in the film that almost got cut?

J: not really if anything we had too many jokes & it was kind of hard to decide which take was better !

H: Yes, certain producers wanted the balcony scene cut, but I insisted it stay in because it shows that women can be just as smart as men when it comes to the manipulative game of love. I also knew this was the scene where the men get busted for their pick up line antics. I love this scene because it balances out the movie showing both genders being smart about the game of love. So yeah, I’m glad I fought to keep that scene in.

Q: After living with these characters for so long, what do you think they’d say about modern dating techniques.

J: haha, well good thing is most everyone knows what a Wingman is from the moment they hear the word – I’ve been one for friends, heck I think we all have at one point or another

H: Ha, that it’s a mess, it’s always a mess, right up until the point that it’s not, and you finally find that right person and it becomes the most beautiful thing in the world. And then all the bad stuff goes away! That’s the trick: stay in it until it works, even if means you have to hire a crazy Wingman to help get you there, HA!!!