Plot
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. Chelsea has forgotten her audio recorder, so they first go to her apartment. While there they discuss a magazine article about the Cinderella complex. Chelsea explains that Cinderella left something behind to let the prince know that she wanted to see him again.
Andre is attempting a foray into serious films with Uprize, in which he portrays Haitian Revolution figure Dutty Boukman, and is sensitive to criticism, particularly by Times critic James Nielson, whose previous reviews of his 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. When Jazzy refused to pay them, they contended they were raped, leading to Andre's arrest and subsequent sobriety.
The limo gets hit by a cab, so Andre and Chelsea wander the city. He stops to pick up the rings for his wedding to reality-TV star Erica Long. Following a subtle, tense interaction with Andre assisting an acquaintance who is actually his father, they visit the apartment of his old friends and ex-girlfriend.
Chelsea interviews each, learning that Andre wasn't particularly funny when he started doing stand-up. They nominate their five favorite rappers, including a sixth as well. Andre goes to radio shows such as Opie and Anthony to promote Uprize and attends a press conference with fellow stars Taraji P. Henson and Gabourey Sidibe. To his chagrin, Andre is asked about the next Hammy movie.
At a hotel, Andre and Chelsea unexpectedly encounter her boyfriend, Brad, along with his friend Ryan, who is wearing Brad's shirt. she 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 they end up kissing.
Andre asks to borrow Chelsea's phone, as his own died. While using it, he sees an email from her editor, revealing she is James Nielson. 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.
In jail, Andre calls Erica, who fumes over the arrest, mainly because of how it will look for her image. She tells him 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 Hammy The Bear theme. There, Andre hangs out with Jerry Seinfeld, Adam Sandler, and Whoopi Goldberg, who give him different views on marriage and sex. Chelsea finds him there, wanting to make it up to him.
Andre, Chelsea, and Silk go to the Comedy Cellar, where Andre gets up onstage and performs standup for the first time in years. He's still funny, and the crowd loves him. Afterwards, he tells Chelsea he got inspired after being in jail and talking to DMX, who told Andre he does not want to keep rapping and wants to sing instead. DMX then sang "Smile", terribly.
They drop Chelsea off at home, where she and Andre share one last kiss. He asks for 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, and Silk smiles.
After the credits begin rolling, the movie returns to the party, where Jerry Seinfeld shares his "top five" as Sugarhill Gang, Eminem, Wale, Ice Cube, and Sir Mix-a-Lot.
