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If Chris Rock's first feature writing/directing effort, 2003's election-themed Head of State, while showing some flashes of his whip-smart wit, overall felt him a bit forced into a more lowest-common-denominator-appealing package; and his next, 2007's underrated I Think I Love My Wife, had him indulging perhaps too strongly in his artier interests and influences (in this case, the work of French auteur Eric Rohmer) for mainstream tastes, then Top Five finds him finding the perfect balance: that between an observant, often scathing, satire of the entertainment biz and an appealing and understated romance, all in one sometimes outrageous, often hilarious, wide-appeal entertainment package. Rock's indie-leaning cinematic sensibility shows through in the film's basic framework, which is essentially one day-long conversation all around New York City between stand-up comic-turned-film star Andre Allen (Rock) and journalist Chelsea Brown (Rosario Dawson) conducting an interview timed to the release of his latest movie, a change-of-pace, gravely serious, historical drama. As is the norm of such walking-and-talking films, a traditionally constructed storyline is distinctly secondary to character-driven discourse, for what begins as a typical interview give and take becomes something more intimately and mutually revealing.
In terms of narrative trajectory, the above is hardly fresh nor terribly exciting in concept. However, as is just as usual with films of this ilk, the effectiveness and appeal lies not in plot but personality--or, even more so in this specific case, point of view. Whether directly confessed or gleaned through anecdote, a number of astute observations, pointed opinions, and piercing insights about film franchises, typecasting, all of Hollywood in general, and the world at large are made, which, while related in character as Andre, are quite obviously the writer/director's own, delivered with the same brutally frank bite as he famously does on stage. Keeping this from coming off as ridiculously self-indulgent is how Rock has an equally well-rounded counterpoint character in Chelsea, and an equally dialogue-dextrous leading lady in Dawson, whose naturally radiating warmth and intelligence has rarely been served as well as it does here. That Andre and Chelsea's meeting is just as much one of their minds as it is their hearts goes a long way toward selling the whirlwind, single-day courtship contrivance.
Also downplaying the de rigueur routine rom-com touches and obliterating any hint of overly syrupy sentiment is just how laugh-out-loud funny the film frequently is, and that is due in large part to Rock's rather ironic generosity to his supporting cast. While largely a two-character piece, the film also makes room for a vibrant ensemble of characters, whether through literal detours in Andre and Chelsea's travels or through flashbacks. Many familiar faces such as Gabrielle Union, Cedric the Entertainer, Kevin Hart, Romany Malco, Jerry Seinfeld, Taraji P. Henson, and Tracy Morgan turn up in roles ranging from cameos to more full-fledged supporting roles, and everyone makes sure to not waste whatever screen time they have and make memorable impressions, also in varied ways, from riotous (most notably, Cedric) to unexpectedly cutting (Union, as Andre's reality TV star fiancée).
Much like how the wide canvas of characters impress individually while still illuminating the core concern, so do the loose storytelling and episodic rhythms of Top Five ultimately congeal into a cohesive whole. In encompassing all of seemingly disparate passions and perceptions, from hip-hop to comedy, to the craft of performing to the reality of business, to the pain of regret to the joy of discovery and rebirth, Rock has made an entertainment that is not only a wild and rich study of his lead character but the character of the filmmaker himself.