Boys on the Side is a 1995 comedy-drama film about friendship, written by Don Roos and directed by Herbert Ross.

Three unique women embark on a cross-country road trip: Jane (Goldberg), a lesbian lounge singer in search of a new life; Holly (Barrymore), a pregnant girl who just wants to escape her brutal boyfriend; and Robin (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 drive across country to California with. Jane answers the ad and agrees to join Robin after her car gets towed during their meeting. Jane and Robin leave New York 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. Unbeknownst to the women, without medical attention, the blow Nick received to his head turns out to be fatal, as he stumbles across the floor and dies.

The three unlikely travelers then form a special friendship on their journey which sees them through ultimately tragic times.

After discovering that Holly accidentally killed Nick and that she 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 (McConaughey), and Robin finds the courage to face her impending death. Shortly after Jane and Robin have a falling out over Jane telling a guy (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 a telling scene inside the Allegheny County Courthouse "Bridge of Sighs" with Robin and Jane making peace with each other.

The movie features some great shots of downtown Pittsburgh and the vistas from Mt. Washington in the city as well as the gothic architecture of the courthouse and "Bridge of Sighs".