Caught Up 1998

Daryl Allen [Bokeem Woodbine] is an ex-con trying to turn his life around. He dreams of opening a nightclub and being part of his son Jerome [Shedric Hunter Jr.]’s life. When his friend Trip [Damon Saleem] offers to lend him the money to get the club started, Daryl agrees and drives Trip to the bank, unaware that Trip is taking part in a robbery. A police chase ends in a fiery car crash: Trip is killed, and Daryl is sent back to prison.

After five years, Daryl is released and learns that his girlfriend Trish [Cynda Williams] has married and moved away with their son. At first, Daryl reconnects with life on the outside and meets his parole officer, Jake Samples [Tony Todd], who warns that any trouble could land him in prison for 25 years to life. Daryl also encounters Vanessa Dietrich, a psychic who looks exactly like Trish. Vanessa [Cynda Williams] develops a wary rapport with Daryl, and they seem to click, though a masked gunman soon shoots at them. Vanessa hands Daryl a gun to defend himself, and they spend the night together, starting a complicated web of danger around them.

The morning after, Daryl wakes to find a gun pointed at his head by Vanessa’s friend Billy [Joseph Granda]. Billy explains the weapon is loaded only with tests, but the tension remains high. Vanessa explains that she has recently secured Daryl work as a limo driver, and although he initially resists, he eventually accepts after meeting Herbert [Clifton Powell], who works for Billy. Vanessa also gives Daryl a tarot reading that seems uncannily accurate about his life.

Daryl and Vanessa go to a club, but as they leave, the masked gunman reappears and shoots at them again. Daryl wonders if Vanessa is involved, while she blames her ex Ahmad [Basil Wallace] for the danger. He tries to stay away, but trouble finds him once more.

Billy asks Daryl to deliver a car for a client. The car has a flat tire, and when Daryl retrieves the spare, he discovers a dead body in the trunk. A police officer approaches, and as the trunk is opened, Daryl weighs his options and briefly contemplates striking the officer to avoid a life sentence. The officer closes the trunk, unaware of the body inside.

Daryl goes to Billy’s office, beats him up, and quits. On the way home, he is arrested. Herbert reveals himself to be a cop named Frank Lowden, who has been investigating Billy for months, and he urges Daryl to keep working for Billy under supervision.

Daryl confronts Vanessa and demands the truth. She explains that her ex, Ahmad, gave her a diamond worth half a million dollars, which is why she’s in danger. Though reluctant, Daryl spends the night with her again. The next morning, he wakes with blood on his hands and finds Vanessa murdered. The police arrive, but he escapes through a window.

Armed with a gun, Daryl goes to confront Billy about Ahmad. Billy denies knowledge of Ahmad and is assaulted by Billy’s men, but Daryl hides in a closet. Ahmad arrives—this time revealed as a Jamaican mobster—and later questions Billy about Daryl’s whereabouts, since Daryl is wanted for Vanessa’s murder. Ahmad discloses that Vanessa helped him steal a diamonds shipment, but she betrayed him by taking the diamonds and disappearing.

Ahmad shows Billy a diamond and presses for Daryl’s location. Billy tells him that Daryl is in the closet, but Ahmad misreads the situation and an acid attack intended for Billy ends up killing him. The other bodyguard checks the closet and fails to spot Daryl above him.

Daryl decides to leave town and calls Trish’s husband, Roger [LL Cool J], who explains that he and Trish had a fight and she’s been gone for over a week. Daryl then speaks to his son Jerome [Shedric Hunter Jr.] and urges him to stay out of trouble, realizing he may never be part of his child’s life. On the road, Daryl has flashbacks and returns to Los Angeles. At Vanessa’s grave, he digs up her body and is shocked to discover it is actually Trish.

Daryl tracks Lowden to a house, where he finds Vanessa alive but involved in a dangerous ruse to escape Ahmad by faking her own death. He wants to turn Vanessa in, but Lowden—who is in on the scheme with Vanessa—knocks him out and cuffs him. Ahmad arrives to confront them, and a fierce shootout erupts. In the darkness, a lamp is knocked over and chaos ensues, leaving everyone dead except Daryl. Before Vanessa dies, she tells Daryl that she loves him. He pockets a bag of money and phones Jake from a payphone to explain the chain of betrayals. Jake reveals that Ahmad didn’t know where Vanessa was after her “death” and implies someone else was the shooter. A distant crash suddenly knocks Daryl unconscious.

When he regains consciousness, the threatening gun is aimed at him by the man who was Trip’s bank-robbery partner—the former bank security guard—now stalking Daryl to avenge Trish’s death. Daryl fights back, is shot, and falls into the water, where the guard commits suicide. Daryl survives, protected by a bulletproof vest.

With the money from Vanessa, Daryl becomes the owner of his own club, and Jerome joins him to start a new life. The film closes with Daryl voicing a hard-earned philosophy: Life is just a game, but to win you gotta avoid getting caught up.