Reporter Chelsea Brown (Rosario Dawson) spends a pivotal day interviewing comedian and recovering alcoholic Andre Allen (Chris Rock), known for his role in the popular film series Hammy The Bear, centered around a cop in a bear suit. As Andre attempts to transition into more serious roles with his latest film Uprize, where he portrays the Haitian revolutionary figure Dutty Boukman, he becomes disheartened by the negative critical reception, especially from James Nielson, a prominent critic from the New York Times, whom Andre despises.
To salvage his image amidst a lack of offers, Andre's agent Charles (Kevin Hart) persuades him to participate in this interview with Chelsea, who also works for the NYT. Initially starting the dialogue inside his luxurious limousine, Andre reflects on a dark chapter in his life from 2003 in Houston, where a fateful encounter with Jazzy Dee led to a spiral involving drugs, alcohol, and an unfortunate arrest stemming from a misunderstanding with some women.
As the conversation unfolds, Chelsea steers it towards Andre's impending marriage to TV celebrity Erica Long (Gabrielle Union), which is only three days away. Andre, however, shows little enthusiasm about discussing this topic. A sudden mishap occurs when their limousine gets struck by a cab, prompting the duo to navigate the city's streets together. They make a stop at a jewelry store, where Andre is devastated to learn that Erica has altered their wedding rings to appease her television crew, desiring more "classy" options.
Their journey continues to the apartment of some of Andre's old friends and his ex-girlfriend, where each adds their perspective on his stand-up career, candidly expressing that he wasn’t always the funny man he is perceived to be. Conversations flow about their mutual appreciation for hip-hop, blending humor with nostalgia. Andre also attempts to boost his film’s visibility through various media appearances, including on popular shows and press conferences, where he is inadvertently reminded of his origins—especially when asked about the next Hammy installment.
As the day progresses, Andre and Chelsea cross paths with her unfaithful boyfriend, Brad, unveiling a series of personal revelations. This leads to a moment of intimate connection between Andre and Chelsea, culminating in an unexpected kiss. However, the mood shifts dramatically when Andre discovers through Chelsea's phone that she is, in fact, James Nielson's target. This revelation leaves him feeling hollow, prompting a bout of despair that lands him in jail.
In a heated conversation with Erica, she expresses frustration over the fallout and the potential blow to her public image. Under pressure from Erica's manager to preserve their public profiles, Andre's world of fame takes a strange turn during his bachelor party, themed after Hammy The Bear. There, surrounded by industry legends like Jerry Seinfeld, Adam Sandler, and Whoopi Goldberg, Andre receives varied opinions on relationships and commitment, while Chelsea waits to reconcile with him.
Ultimately, after a surprise stand-up gig at the Comedy Cellar stirs something within him, Andre realizes his comedic talent is still alive. Conversations with Chelsea during their emotional goodbye provoke thoughts of ambition and missed opportunities. Now fueled by inspiration and a deep yearning for connection, Andre re-evaluates his choices as someone in the entertainment world, hinting at unforeseen paths as he grapples with his identity amidst the pressures of fame and personal turmoil.
