There is a very specific kind of funny that David Wain does better than anyone working in comedy right now, and it is nearly impossible to explain to someone who hasn't seen it. It's the kind of humor where a joke lands not because it's clever but because it is so completely, specifically stupid that you can't help but respect it. Gail Daughtry and the Celebrity Sex Pass is that kind of movie, and it is genuinely one of the funniest things I've seen in years.
The premise is exactly what the title suggests. Small-town hairdresser Gail Daughtry gets her heart broken when her fiancé actually follows through on their celebrity sex pass agreement, sleeping with Jennifer Aniston at a book signing in what becomes one of the best comedic inciting incidents in recent memory. Gail, played by Zoey Deutch with this infectious, corn-fed sincerity, decides the only logical response is to fly to Los Angeles with her best friend Otto and track down Jon Hamm. From there, the movie becomes a full-on Wizard of Oz riff through Hollywood, complete with a ragtag crew of misfits, a mob subplot involving a missing briefcase, and a string of celebrity cameos that I genuinely do not want to spoil.
The cast Wain and co-writer Ken Marino assembled here is absurd in the best way. John Slattery plays himself as a man apparently living in someone's garage and taking up martial arts because work has dried up. Richard Kind shows up as a cab driver. The cameo list runs deep, and every single one of them earns their moment. What makes Wain so good at this, going back to Wet Hot American Summer and They Came Together, is that the jokes are never random for the sake of random. There's a rhythm to how this kind of absurdism is deployed, and Wain has spent twenty years perfecting it.
Deutch is the reason this movie holds together as well as it does. She is one of the most underused comic actresses out there, someone who can play genuine emotion and total chaos in the same breath, and Gail gives her room to do both. If you haven't seen her in Buffaloed or Not Okay, fix that before or after you see this. She's been quietly building toward a lead role this good for a while now.
Honestly, skip the trailer. It cannot do justice to what this movie actually is, and a couple of the best bits would be half-ruined by watching it. Just find a showing, bring a friend or two, and give it your full attention. This is the kind of comedy that rewards you for actually showing up.
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