I can remember an office my wife worked at long ago. Prominently placed was a sign that read, “If less than three people laugh, it’s not funny.” Some of the folks employed there were very kind, some were there simply to punch a clock, and one was unintentionally hilarious.* With the exception of the head of the company, who possessed both a love of horror movies and a deadly wit, most of the people who worked there were not funny. Clearly, they didn’t heed the sign. 

The people in that office forgot the old saying, that while dying is easy, comedy is hard. It requires timing, intelligence, and fearlessness. And even then, if you’re witty, you’ll eventually slam up against someone that you cannot make laugh. You’ll make a joke. They’ll cock their head in confusion like Michael Myers. You’ll probably follow up with another joke, and it’ll have the same effect as if you started speaking in Turkish, a kind of baffled confusion. The situation sucks for them, and it sucks for you. 

I love comedies, and finding something funny is like falling in love. Sometimes it hits just right, and when it does, you’ll follow it anywhere. When it doesn’t hit? That’s when things get complicated, and I’ll sit there dead serious as goofy shenanigans unfold before me. I had that experience watching Wing Man, a comedy made by one of the great improvisers, and it made me laugh less than a handful of times. It begs the question, is the problem the movie or me?

We’re introduced to Turk (Harland Williams), a very particular man with a very particular profession. He’s a professional wingman, and his motto is, “If you don’t get laid, I don’t get paid,” so you can imagine what he does for a living.

At a bar, Turk spots his next potential client. That would be Bob (Evan Marsh), a midlevel business dude celebrating his upcoming wedding. The only problem being, Bob kind of sucks at being a partner. He’s not a bad guy, he’s just oblivious, except for when the script needs him to have self-awareness. As Bob downs shots like it’s his first time at Senor Frog’s, his fiancee Terri (Shiva Negar) wonders if she’s making a mistake. She makes her decision when she falls for Kazzim (Russell Peters), and just like that, the wedding is off. 

Turk discovers that Kazzim has enlisted the services of rival wingman, Eddie (Jamie Kennedy). Eddie and Turk are the best of enemies, and Turk swears vengeance. He does so, in his weirdly particular way, by offering his help to Bob. The plan, such as it is, is for Turk to teach Bob the finer points of wooing the opposite sex. Or get him back together with Terri. Or both, because YOLO.

Harland Williams has been involved in the comedy scene since the mid-80s, and has been in a lot of film and television since the 90s. He’s one of the greats at improv, and we know that because of his ability to grab attention within a single scene.** As a director, he’s not bad. Considering that Wing Man had a modest budget, Williams makes the most of what he has. The film never looks cheap, and Williams is able to create some…um…let’s go with memorable moments, such as a makeout session interrupted by a rapey koala. My only real issue with the filmmaking is that the film frequently drags, and sluggish pacing like that is deadly for a comedy. 

Speaking of comedy, let’s talk about the screenplay by Williams. It’s got a couple of serious problems that, had they been resolved in rewrites, would have ultimately made the film a better one. The first issue is that the script starts in the wrong place and focuses on the wrong person. We’re told Bob needs to learn rizz, yet his breakup with Terri feels like it comes out of nowhere. It would have been smarter to focus the script’s POV on Bob. By doing that, we get a better sense of why Bob failed in the first place and why he needs the Wing Man. Plus, it turns Turk into a supporting character, which is a benefit. My second issue is that many, many of the jokes feel like they’re the product of in the moment improv or a first draft. They’re often lazy, obvious, or random. As a result, most of the surprise vanishes.*** There are so many times where the gags felt like products of raunchy comedies from the 90s, and there were so many times where I shrugged when I should have been guffawing.

The cast is okay, and there’s one member of it who should have had more opportunities to cut loose. For a role like Turk to pop, I think one of two things needs to happen. First, you need to cast someone like Jack Black, an actor overflowing with charisma. You do that and you’ll understand why Turk is able to get away with so much. Or second, you cast someone with anti-charisma, and have a running joke that this guy is inexplicably a magnet, and that fact drives people around him nuts. Williams leans harder into Turk’s anti-charisma, yet never does anything surprising with that concept. There’s another smarter, weirder movie where Turk is revealed to be brilliant, calculating, and a keen student of human behavior. An approach like that would have been genuinely off the wall, plus it would have allowed for more mockery of the dating scene, past and present. Evan Marsh does nice work as the romantic lead, Bob. He’s got the chops to play a put-upon guy who needs to learn a lesson. The problem is, the script often veers between Bob being an idiot and Bob being a sad-sack, with the only consistency being that he has to deal with Harland Williams’ madness. Marsh can handle that; I just wished his character had more to him. 

An awful lot of the raunchy 90s comedies were extremely dude-focused. So much so that the guys were the ones who got to be funny, while women were either called upon to be hot or old or fat. This film does that, and it wastes the talents of Kayla Wallace. She plays Holly, Bob’s executive assistant, and as the film goes on, we start to see an attraction develop between the two of them.**** For the most part, Wallace plays a character who’s sweet and supportive of Bob. Yet a few times during the film, Wallace’s Holly gets to go bonkers. She’s good at that, playing someone with a river of insanity bubbling just under the surface. The film makes a major unforced error by not consistently allowing her to be funny, which makes it a perfect throwback to 90s comedy.

If you’re someone who vibes with the older Happy Madison comedies, odds are you’ll have a nice time with Wing Man. That audience is mostly guys in their late 40s and up. Like me, yet I bounced off this movie like a bug and a windshield. It doesn’t really matter. Like that long ago sign in my wife’s office, this movie will make more than three people laugh.

*Some of my favorite people to listen to are those who are confident and totally lack self-awareness. 

**Williams hit the height of his career in the 90s & had memorable moments in films like There’s Something About Mary. Since then, he’s worked steadily. 

***If you want a comedy that’s impossible to predict, see I Love Boosters as soon as humanly possible. 

****An obvious HR nightmare, and a more clever comedy would have found ways to mock that.

Tim Brennan Movie Critic

Tim has been alarmingly enthusiastic about movies ever since childhood. He grew up in Boulder and, foolishly, left Colorado to study Communications in Washington State. Making matters worse, he moved to Connecticut after meeting his too-good-for-him wife. Drawn by the Rockies and a mild climate, he triumphantly returned and settled down back in Boulder County. He's written numerous screenplays, loves hiking, and embarrassed himself in front of Samuel L. Jackson. True story.