Nothin' 2 Lose (2000)

When his fed-up girlfriend gives hip-hop producer Kwame Gatmon a 30-day window to marry her, he must transform himself from hard-partying bachelor into serious musician, basketball star and more creative lover. Unless he can convince his longtime ladylove that his swingin' single days are over, he's liable to end up alone. The film marks the directing debut of Barry Bowles, who makes a cameo appearance.