Watch Outing Riley

Outing Riley is a dramatic comedy released in 2004 directed by Pete Jones. The movie revolves around 28-year-old Bobby (Pete Jones) and his two friends, Amie (Jenny Mollen) and Andy (Benjamin Arthur), who plan to take Bobby's closeted older brother, Riley (Nathan Fillion), on a wild night out in Chicago's Boystown, a famous gay neighborhood.

Bobby is a struggling playwright, who feels that Riley, his older brother, is living a double life. Riley is a successful lawyer who has a fiancee and a reputation to keep, but deep down, he is gay and hasn't come out to his family yet. Bobby, Amie, and Andy plan to help Riley come out to the world by taking him out to a night of partying, drinking, and dancing in the gay bars of Boystown.

The movie opens with Bobby visiting his therapist, played by Stoney Westmoreland. Bobby reveals that he has a history of depression and that his brother's closeted life is affecting him. The therapist advises him to accept his brother for who he is and let him come out when he is ready.

The trio starts their night at a local pub, where Bobby bumps into his ex-girlfriend, who is now dating Amie, causing tension between the two. They then proceed to a drag show, where Riley is reluctant to participate, but the queen on stage encourages him to join in. This marks the beginning of Riley's transformation from a conservative lawyer to a flamboyant gay man, confident of his identity.

As the night progresses, Bobby, Amie, and Andy continue to try to make Riley feel comfortable in his own skin. They take him to a gay dance club, where they meet a group of Riley's coworkers, who think he is Bobby due to some confusion between the two. This leads to a hilarious moment when Bobby is mistaken for Riley and nearly outs himself to his brother's colleagues.

As the night winds down, Riley becomes more comfortable with his sexuality but begins to worry about coming out to his family. Bobby then has a heart to heart with his brother, persuading him to come out and face his fears. The brothers share an emotional moment, and Riley finally feels comfortable enough to come out to their father, who is played by Michael McDonald.

Outing Riley is a touching portrayal of family, acceptance, and coming out in a society that is quick to judge. The movie tackles serious themes with humor and sensitivity, striking a balance between the two. The performances of the cast are commendable, with Nathan Fillion delivering a standout performance as the closeted lawyer struggling to come out to the world.

Overall, Outing Riley is an excellent movie that explores the complexities of coming out, family dynamics, and identity. It is a must-watch for anyone who appreciates a good coming-of-age story and a heartfelt portrayal of human emotions.