He's My Girl (1987)

Best friends Bryan and Reggie are in the music business in Missouri. When Reggie enters Bryan into a contest for a chance to go to L.A., Bryan wins the contest and wants to bring Reggie with him; however, Bryan must bring a girl. To make sure Bryan gets his shot, Reggie decides to pose as a girl. When the duo arrive in L.A., they fall in love with two women, and they must also stop the contest's promoter when he steals Bryan's song for his star, Simon Sledge.