Boys on the Side

Boys on the Side is a 1995 American comedy-drama film directed by Herbert Ross (in his final film as a director). It stars Whoopi Goldberg, Drew Barrymore, and Mary-Louise Parker as three friends on a cross-country road trip. The screenplay was written by Don Roos.

Plot
Jane (Whoopi Goldberg), a musician who has undergone a break-up with both her girlfriend and her band, decides to move from New York City to Los Angeles for a new gig. She answers a newspaper ad for a traveling companion from Robin (Mary-Louise Parker), a real estate agent who's also looking to move to California. Thinking Robin's a square, Jane initially declines to join her, but agrees after her car gets towed. Jane and Robin leave and make a stop in Pittsburgh to see Jane's friend, Holly (Drew Barrymore).

Jane and Robin stumble across a fight between Holly and her abusive boyfriend, Nick (Billy Wirth), over some missing drugs. As the three women work together against Nick, Holly hits Nick in the head with a bat to stop him from attacking Jane, knocking him out. The three bind Nick, who regains consciousness, to a chair with tape and leave. Hours later, Nick frees himself from the chair, falls and hits his head on the bat and dies. The three women form a special friendship, and after learning that Nick is dead and Holly is pregnant, all decide to continue to California together.

During a stop in Tucson, Arizona, Robin has to be hospitalized for pneumonia, at which point Jane and Holly learn she has HIV. The three decide to stay in Tucson and start new lives there. Things are cheerful for a while, as the three live together and Holly falls in love with a local police officer (Matthew McConaughey) named Abe Lincoln. Jane has an unrequited crush on Robin, and Robin tenderly buys Jane a piano.

However, things fall apart. Jane and Robin's friendship crumbles when Jane, well-intended, tells a friendly bartender (James Remar) interested in Robin that she has HIV. Feeling betrayed, Robin asks Jane to move out. When Abe proposes to Holly, Holly tells him about Nick and he arrests her, despite still intending to marry her. Holly is taken back to Pittsburgh to stand trial for murder. Jane and Robin also return to Pittsburgh and make peace with each other in the courthouse. Holly takes an offer of involuntary manslaughter with one to two years in prison. Robin collapses after the trial from a lung infection, and in the hospital, Jane and Robin confess how they loved each other.

Time passes, and Holly is free and living happily with Abe and her daughter, who Abe has adopted. Robin is now in a wheelchair, very far along with AIDS and not expected to live much longer. At the party, Robin weakly begins to sing the Roy Orbison song "You Got It" as a reference to her first conversation with Jane, and Jane gently finishes the song. In the final scene, Robin has died from AIDS, Holly and Abe plan to stay in Arizona and raise a family, and Jane hits the road to seek a new life in Los Angeles.