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Chris Rock stars as Andre Allen and Rosario Dawson appears as Chelsea Brown in “Top Five”. (photo courtesy of Paramount Pictures)

Any film in which Jerry Seinfeld makes it rain is a keeper, even if Chris Rock runs the show. Strike that — I applaud Rock for “Top Five”, the most surprising and heartfelt comedy of the winter season. He might not be a stellar actor, but as leading star, director and screenwriter, something unforgettable results, especially with Jay Z in the producer’s chair.

Once upon an improv club, Andre Allen (Rock) was funny and truly inspired. Unfortunately, years of boozing led such a promising star astray. But now he’s sober, and so too his humor. Freed from his stand-up and comedy flick days, Andre just wants to be taken seriously, but that won’t happen with his latest attempt, “Uprize”, which depicts the greatest slave rebellion in history.

In all fairness, it’s about time we see thousands of white people killed on screen — a nice counterpart to the ludicrous millions of non-whites decapitated in historical flicks like “300” – but audiences seem to care more about the next mindless Madea adventure.

No one cares what Andre thinks as his personal life eclipses due to impending nuptials with fiancé Erica Long (Gabrielle Union), who channels Kim Kardashian in uncomfortably close ways considering Kanye West co-produced “Top Five”. So Andre has one last chance to escape his joke of a career: an interview with Chelsea Brown (Rosario Dawson) for The New York Times, a publication that panned every one of his films.

In the spirit of their AA recovery, the interviewer and interviewee decide on a painful truth. Andre unclothes his most embarrassing secrets and most vulnerable moments: hitting rock bottom, coping with a mooch of a father and caring for old friends when his “bae” (and I use that term with all the idiocy built into it) favors camera-ready celebs instead. So Chelsea shadows Andre on the opening day of “Uprize”, less than 24 hours before he must tie the knot.

“The Congress”, “Birdman” and now “Top Five” –– this is the third film in 2014 that allows its leading star to ponder an actor’s life once the A-list is out of sight. “Top Five” is reminiscent of “Birdman” in many ways: an actor haunted by a blockbusting character he just wants to forget, a failed attempt to change public perception of his artistic diversity and a personal life stripped apart by the camera’s panoptic gaze.

Perhaps more interesting though, “Top Five” looks to hope. Dawson, as a young, artistic writer and critical thinker, reminds Rock’s Andre what life could and can be. Her poor life choices are exposed as the day goes on and help Andre navigate his own insecurities while helping her through the rubble of some awful suitors. It’s all refreshingly vulnerable, unlike much of Rock’s usually bland genre films.

Say what you will about Rock’s countless terrible movies (namely both “Grown Ups”), but his long tenure in the business is more than commendable. “Top Five” critically reflects on three decades of stardom. But this isn’t just about him. Thanks to cameos and bit parts by Kevin Hart, Sherri Shepherd, Cedric the Entertainer, Tracy Jordan, Gabourey Sidibe, Jay Pharoah, Adam Sandler, Whoopi Golberg, DMX and Leslie Jones among others (he cashes in on quite a few favors), he engages Hollywood, stand-up and especially the hip-hop industry in rich ways. (The primary shtick of the film is, “Who are your top five?”)

The painful truth is that Rock isn’t a great actor. He commanded attention alongside “SNL” alums Adam Sandler and Chris Farley at the start of the 1990s, but his abilities as a serious performer are highly suspect, even here.

Yet there’s something to be said about a film so well written and directed that it warrants a level of forgiveness for the 49-year-old writer/director’s stiffness on screen. He might feel out of place, but he knows how to surround himself with great co-stars like Dawson and the always zany, J.B. Smoove, as his security guard, assistant and best friend.

This isn’t a film you expect to enjoy, and for the first 20 minutes, you’ll easily be on the fence about it all. But it’s a slow burn that ignites into something charming, authentic and eventually quite humorous. You’ll cringe more than laugh thanks to some rather raunchy, hilarious scenes, but the relationship between Chelsea and Andre is something wonderfully akin to Cinderella.