Chris Rock mines his history as a comedian-turned-actor for the hilarious Top Five

“What’s your top five?” is the question that triggers the characters of Top Five to excitedly announce their five favourite hip hop acts. Someone includes Ice Cube in his list, which leads to uproarious laughter and irreverent yelling. This question is kind of like a party trick: it initiates the conversation, while also maintaining a distinctly chill demeanour. This is what makes Top Five tick: the film is hilarious and whip smart, while also cool and composed. Written, directed by and starring Chris Rock, Top Five is undeniably Rock’s best work in recent times.

Rock plays comedian-turned-film-star Andre Allen, who after a string of Hollywood hits as Hammy the Bear, wants to be “taken seriously”. Unfortunately, his new movie as a Haitian slave revolutionary looks bound for box office disaster and his upcoming televised wedding to reality star Erica Long (Gabrielle Union) comes at a hefty price. Journalist Chelsea Brown (Rosario Dawson) trails Allen for a piece for a day and they eventually trade stories while walking around the city, shedding insight into Allen’s personal history and career journey.

While Top Five has been frequently alluded to Woody Allen or Louis C.K., the New York in Top Five quite evidently resembles another movie Rock has starred in — Julie Delpy’s excellent Two Days in New York. Like Delpy, Rock situates the streetscapes of the city as the battleground for two opposing forces. Delpy situates her French heritage, represented by her real-life loud crass parents, against her American lover played by a charming, easy-going Rock. Similarly, in Top Five, Allen and Brown walk down the city streets, spouting amusing, cheeky anecdotes while also highlighting their keen racial awareness as a person of colour living in New York. This is also the strongest feature of Top Five — the relaxed storytelling and the laidback, strolling camera versus the hijinks and madcaps of the film’s narrative makes for a riveting cinematic experience. That is, until you get distracted by the celebrities.

Top Five is like a roll-call for famous African-American entertainers: there’s Tracy Morgan, Cedric The Entertainer, J.B. Smoove, Sherri Shepherd, Romany Malco, Kevin Hart and a scene-stealing cameo by DMX. One highlight is during Allen’s bachelor party where Adam Sandler, Jerry Seinfeld and Whoopi Goldberg give Allen some marital advice. Seinfeld is at his most Seinfeld-esque and Sandler is refreshingly earnest. In another moment where Allen hangs out with his close friends, Rock recruits black SNL cast members like Tracy Morgan, Leslie Jones, Michael Che, and Jay Pharoah (did someone not give Kenan Thompson the memo?). The entire scene feels like improv, flippant remarks and vulgar comebacks ease through the conversation. Rock certainly did well in calling on his friends — the cast of Top Five is ridiculous and amazing.

Amidst Rock’s latest career moves into Madagascar and Grown-Ups, Top Five come as a very pleasant surprise. The film’s semi-autobiographical nature is very endearing, which makes Top Five so unique in Rock’s recent repertoire. For example, Top Five is chiefly backed by Jay-Z and Kanye West’s “N*ggas in Paris” (who are also co-producers), and it feels more like a song that Rock really, really likes rather than music that works best for his movie. Overall, the film involves Rock putting together things he is a huge fan of anyway — good stand up, great company and excellent hip hop — which makes Top Five a truly enjoyable ride.

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