Roland is getting married and is currently missing. Slim, who scoffs at the idea of marriage, is furious at Roland for disappearing. The story flashes back to Mike as a youth when he first encounters Roland and Slim, his first real crush on a girl Alicia, and the three young men's misadventures as teenagers growing up in 1980s Inglewood, California. Shy and awkward, Mike is quickly befriended by Slim and Roland. On a dare from Slim and Roland, Mike reluctantly grabs Alicia's butt, leading to a physical altercation with her older brother Stacey, a Blood gang member. While he is beaten up, Mike earns Stacey's private respect for having courage to fight back. Meanwhile, in present day, Mike and Slim get a call from Tanya, an ex-girlfriend of Roland's, saying that Roland is at her house, extremely drunk. When they arrive, they argue with Roland for putting his relationship at risk, as the wedding is just hours away. Flashing back to the '80s, the boys are on their way to the first dance of the year, stopping at a convenience store that gets held up by Stacey. Stacey recognizes the boys and offers them a ride to the dance. The group is nearly arrested after being pulled over for a broken tail light. Mike's quick thinking prevents one of the cops from finding Stacey's gun and they are let go when the cops respond to a call about the stick-up Stacey and his friend just committed. Impressed, Stacey begins a new friendship with Mike by apologizing for their prior run-in. However, he explains that he was protecting his sister, and, seeing how much Mike likes her, gives him advice on how to win her over. When they arrive at the dance, it is almost over, but Mike is able to secure a dance with Alicia and also get her number. Later, Mike and Alicia date for a time before breaking up and remaining friends. In the present day, while reminiscing, Roland becomes sick and accidentally vomits on Slim and Mike. Now, the men only have an hour left before the wedding and they have to get cleaned up, so they take their clothes to the cleaners. Mike, returning to their memories when they were juniors in high school, remembers them thinking about sex, ways to get it and making a lot of bets as to who has it first. Mike has a girlfriend and Alicia has a boyfriend. Despite both of them already being in a relationship with somebody else, one day Mike and Alicia walk to her house from the library talking about the Homecoming dance. They hear If This World Were Mineon the radio, the song to which they had the first dance. Alicia and Mike begin getting intimate, but Alicia stops him and tells Mike to retrieve a condom from Stacey's room. Mike finds a condom in Stacey's room, but before he can leave, has to hide under his bed, so as not to get caught when Stacey and his girlfriend come home. After they leave, Mike goes back to Alicia's room and they finally make love. Mike wins the bet, but he doesn't tell Roland and Slim out of respect for Alicia. It's revealed in the present that after high school, Alicia and Mike went their separate ways. The boys finally make it to the wedding and Roland apologizes to a furious Lisa for leaving her worried. Before the ceremony begins, Mike has a fond exchange with a now-grown Alicia. Roland and Lisa get married. Mike reminisces on the Homecoming dance, declaring that he, Roland and Slim will be the boys from "The Wood."
Cast
Omar Epps as Michael "Mike" Tarver, and he tells the story about how he and his friends grew up together in “The Wood.”
*Sean Nelson as Young Mike, is new from North Carolina, and just moved to Inglewood at a new school and became friends with Roland and Slim.
Richard T. Jones as Laveinio "Slim" Hightower he and Mike help Roland get back to the ceremony to get married.
*Duane Finley as Young Slim, raised up in “The Wood” best friends with Roland growing up and then meeting the new kid on the block Mike. He was always asking for Roland to hook him up.
Taye Diggs as Roland Blackmon he is supposed to get married and has second thoughts about it and is found drunk by his two best friends.
*Trent Cameron as Young Roland, he is hip, fresh, and cool, gets all the ladies, and he gets no play most of the time.
Sanaa Lathan as Alicia, an old childhood friend that grew up and came back to see Mike.
*Malinda Williams as Young Alicia, she was hardcore, but sweet and in time she began to like Mike.
LisaRaye McCoy as Lisa, a bride getting ready to marry Roland, and gets upset about his disappearance.
De'Aundre Bonds as Stacey, and is Alicia's big brother that takes up for her when she is younger. He also is in a gang and reps with the set called “Bloods.” Stacey reappears in the film Dope.
Antwon Tanner as Boo, Stacey's homie and member of the “Bloods.”
The film holds a 61% on Rotten Tomatoes based on 56 reviews, with the critical consensus: "A charming piece of work with believable characters." Reviewing for the Chicago Sun-Times in July 1999, Roger Ebert called it "a sweet, lighthearted comedy" and applauded Famuyiwa for capturing members of the cinematically marginalized African-American middle class. "The movie feels a little uncertain, as if it's moving from present to past under the demands of a screenplay rather than because it really feels that way", Ebert wrote in conclusion. "But the growing-up stuff is kind of wonderful."
Most Performed Songs from Motion Pictures — Joe, Jolyon Skinner: I Wanna Know
Soundtrack
A soundtrack was released on July 13, 1999 by Jive Records featuring rap and R&B music. The soundtrack found great success, peaking at #16 on the Billboard 200 and #2 on the Top R&B/Hip-Hop Albums, and was certified gold by the RIAA on August 25, 1999.
