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New York Times reporter Chelsea Brown is spending a day interviewing comedian and recovering alcoholic Andre Allen, star of the hit film franchise Hammy The Bear, about a cop in a bear suit. He is attempting a foray into serious films with Uprize, in which he portrays Haitian Revolution figure Dutty Boukman, and sensitive to criticism, particularly by Times critic James Nielson, whose previous reviews of Andre's work have been negative and insulting. As the interview begins in his limousine, Andre recalls his lowest point, when he was in Houston in 2003 and met Jazzy Dee, who supplied him with drugs, alcohol and women. Yet after Jazzy refused to pay the women, they contended they were raped, leading to Andre's arrest.
After the limo gets hit by a cab, Andre and Chelsea wander the city. Andre stops at a jewelry store to pick up the rings for his wedding to reality-TV star Erica Long. They visit the apartment of Andre's old friends and his ex-girlfriend. Chelsea interviews each, learning that Andre wasn't particularly funny when he started in stand-up comedy. They nominate their five favorite rappers, including a sixth in their lineups as well. Andre goes to radio shows such as Opie and Anthony to promote Uprize and attends a press conference with fellow stars including Taraji P. Henson and Gabourey Sidibe. To his chagrin, Andre is asked when there will be another Hammy movie.
At a hotel, Andre and Chelsea unexpectedly encounter her boyfriend, Brad, along with his friend Ryan, who is wearing Brad's shirt. Chelsea deduces Brad is cheating on her with Ryan. She and Andre, both recovering alcoholics, stop in a liquor store but resist making a purchase. Chelsea explains in graphic detail how the signs were there that Brad was gay. Andre laughs, calling Chelsea naive. She becomes angry and insults his movie, but the two end up kissing. Andre asks to borrow Chelsea's phone, since his own died. While using it, he sees an email from her editor, revealing James Nielson is Chelsea herself. The truth devastates Andre, who angrily tells Chelsea he felt he was never funny unless he was drunk or high, and now is fearful for his career. Despondent and acting out at a supermarket, he is arrested by police.
In jail, Andre calls Erica, who fumes over the arrest, mainly because of how it will look for her image. She tells Andre this piece of fame is all she has since she thinks she has no other talent. Erica's manager Benny takes the phone and tells Andre to go to his bachelor party for good press and fly out for the wedding. Andre's bodyguard Silk bails out Andre, and they go to a strip club for a bachelor party with a theme based on Hammy The Bear. There, Andre hangs out with Jerry Seinfeld, Adam Sandler, and Whoopi Goldberg. They give him different views on marriage and sex. Andre runs into Chelsea, who wants to make it up to him and invites him to follow her.
Andre, Chelsea, and Silk go to the Comedy Cellar, where Andre gets up onstage and performs standup for the first time in years. He turns out to still be funny, and the crowd loves him. After the performance, he tells Chelsea he got inspired to return to standup after being in jail and talking to DMX, who told Andre he does not want to keep rapping and wants to sing instead. They drop Chelsea off at her place, where she and Andre share one last kiss before departing. Andre asks her her top five rappers, which she lists. While driving away, Silk tells Andre he should have gone after Chelsea. Andre goes through the gift bag from the party and finds items including a scented candle and a bottle of vodka. Then he pulls out a slipper. Andre changes his mind, and Silk smiles.
Back at the party, Jerry Seinfeld shares his "top five" as Sugarhill Gang, Eminem, Wale, Ice Cube, and Sir-Mix-A-Lot.