Boys on the Side
Three unique women embark on a cross-country road trip: Jane (Whoopi Goldberg), a lesbian lounge singer in search of a new life after breaking up with her girlfriend and getting fired; Holly (Drew Barrymore), a pregnant girl who just wants to escape her brutal boyfriend; and Robin (Mary-Louise Parker), an uptight real estate agent who has her own secrets (namely being infected with HIV).
Robin puts an ad in the newspaper that she is looking for a traveling companion to accompany her on a cross country trip to California. Jane answers the ad and agrees to join Robin after her car gets towed during their meeting. Jane and Robin leave New York City and travel through Pittsburgh to take Jane's friend Holly to lunch. They stumble across a knock out-fight between Holly and her abusive boyfriend, Nick, over some missing drugs.
They leave him there bound to a chair with tape after Holly hits him in the head with a bat to stop him from attacking Jane. Later, he frees himself from the chair, stumbles across the floor, falls and hits his head on the bat and dies. The three unlikely travelers then form a special friendship on their journey which sees them through ultimately tragic times.
After discovering that Nick is dead and that Holly is pregnant, the three women decide to continue across country and end up in Tucson, Arizona when Robin has to be hospitalized. They decide to stay in Tucson, hoping to start a new life. However, Jane has a secret crush on Robin, Holly falls in love with and eventually confesses to a local police officer named Abe Lincoln (Matthew McConaughey), and Robin finds the courage to face her impending death.
Shortly after Jane and Robin have a falling out over Jane telling a friendly bartender (James Remar) who was interested in Robin that she has HIV, Holly is arrested by Abe. She is taken back to Pittsburgh to face the consequences of her actions. The return to Pittsburgh involves Robin and Jane making peace with each other on the courthouse's "Bridge of Sighs" while the Pittsburgh Police process Holly.
A few months pass, in Tucson, Holly is free and with Abe and her daughter, which is celebration to all family and friends. Robin is now farther along with AIDS and is not expected to live much longer. The party asks Robin to sing the Roy Orbison song "You Got It" as she performed that song in a Star Search contest; though weak, she manages to sing with Jane backing her singing. In the final scene, Robin has died from AIDS as her wheelchair is now empty, Holly and Abe plan to stay in Arizona and become a family, while Jane hits the road to finally seek a life of her own.
comedy, murder, paranormal, violence, tragedy, romantic