Celebrity “free passes” are one of those relationship games that no one ever really expects to play out. For one, the chance of ever randomly encountering Harry Styles or Margaret Qualley at their local Kroger’s is vanishingly small. And even if one did, would they really have the juice to secure that flirt at 3:27 on Thursday afternoon while in their “today’s a running errands day” clothes? No, for most, the idea of free passes is a silly fantasy game. That’s how Gail (Zoey Deutch) thinks of it when her best friend Otto (Miles Gutierrez-Riley) brings it up at the start of Gail Daughtry and the Celebrity Sex Pass.

Unfortunately, she encounters the rare case of a pass successfully cashed in after a Jennifer Aniston (as a wonderfully matter-of-fact, totally unaware of normal human emotions version of herself) cookbook signing. Gail’s fiancé, Tom (Michael Cassidy), is so taken with the actress, despite never seeing her in anything before, that he switches his pass from Tilda Swinton to her. And a short time later, wouldn’t you know it? To paraphrase Aniston, “Tom’s a real special guy.”

With their wedding only two weeks away, Gail heads west with Otto for a chance to clear her head and meet King of the Whip Curl Remy Fontaine (Thomas Lennon in another one of his heavily accented weirdo roles). Somewhere along the way, the plan changes. Now she’s on the hunt for her hastily chosen pass, Jon Hamm. Maybe if she can bed him, all her newfound doubts will disappear.

The idea of a celebrity “free pass” was popularized by Friends almost 30 years ago (when did I get so old?!) in October of 1996 with the episode “The One with Frank Jr.” Hence, one assumes, the meta-joke of casting Aniston. In other hands, this late-to-the-game device would be eye-roll-inducing. However, in a screenplay by David Wain (who also directs) and Ken Marino and featuring several of Wain’s cultivated troupe of actors, the idea gets a bit more grace. It’s less an outdated reference and more of a vehicle for their singular brand of humor.

The State alums have built a career on films that are out of step with the current moment and better for it. For all that their films flirt with excess—there are a considerable number of bullets fired and punches thrown—there is a gentleness to their work. Time and again, the worlds of their movies prove surprisingly kind and forgiving. They are, more often than not, stories in which the good people are rewarded and the wicked are reprimanded.

Gail Daughtry and the Celebrity Sex Pass, admittedly, doesn’t reach quite the heights of their crown jewel, Wet Hot American Summer, or the arguably “most normal” effort, Role Models. Instead, it lands closer to lesser—but still enjoyable—efforts like They Came Together. At least, that will be the case for established fans.

For newcomers and those less sold on the Wain/Marino style, well, it is a lot harder to say. Will the sheer number of celebrities playing cracked mirror versions of themselves—Hamm and Aniston are joined by John Slattery, Weird Al Yankovic, Elizabeth Perkins, and many more—delight? How about the numerous other former State-ers who pop up in small, strange parts? Will casual moviegoers even notice the allusions to The Wizard of Oz before the closing credits hammer the point home? Will they care?

My best guess is that, like other post-State efforts, there will inevitably be people who just “get” it. They’ll happily embrace Gail Daughtry and the Celebrity Sex Pass—oddly complex plot machinations, “relaxed” pacing, and all. Others will bounce off of it. Hard.

Beneath all the cameos and weirdos is a comedy with a fairly classic structure. It has a sneaky sincerity that steers it clear of just a series of sketches stitched together into a feature. Deutch deserves a tremendous amount of credit for giving the film a strong enough emotional core to make that the case. While I typically think of her as a far tarter performer thanks to the likes of Flower and Buffaloed, she makes Gail a sweet delight that never comes across as caricature. Yes, visiting an authentic Los Angeles hamburger joint—McDonald’s—thrills her. But she’s also unruffled and largely supportive when her bisexual best friend calls for a brief detour so he can get oral sex from a stranger in an alleyway.

For me, it all works from the opening Our Town-esque narration by Frank the Mailman (Fred Melamed) forward. If you’ve ever found yourself on Wain and Marino’s wavelength, this will be another winning ride. If you’ve never understood the appeal, well, Gail Daughtry and the Celebrity Sex Pass won’t spark an epiphany. Wain, Marino, and the rest of their motley crew aren’t making a hostile, elitist film here. But they also don’t worry about changing their tone or eccentricities to make it easy to embrace. To quote the movie itself, they’re keeping it casual and letting things get freaky. Multiplexes and plenty of moviegoers should always have space for that sort of lark.

Choose your celebrity pass wisely before July 10 when Gail Daughtry and the Celebrity Sex Pass arrives in theatres.

Gail Daughtry and the Celebrity Sex Pass Trailer: