Cherry was born and raised in Oklahoma. His father was an accountant which required the family to relocate to California. After graduating from Troy High School in Fullerton, California, Cherry attended California State University, Fullerton's theater program and initially considered a career in performance. After winning $15,000 as a contestant on The $100,000 Pyramid in 1986, he decided to move to Hollywood and pursue writing work. His move came at a bad time; the 1988 writer's strike hit as soon as Cherry arrived. Cherry broke into the industry by working as Designing Women star Dixie Carter's personal assistant.

In 1990, he became a writer and producer for the long-running hit sitcom The Golden Girls. Cherry wrote for the show, and its short lived spinoff The Golden Palace.

When those shows concluded, Cherry co-created The 5 Mrs. Buchanans. The concept of the show centered around the matriarch of the family (played by Eileen Heckart) and the wives of her four sons. The show had a brief run on CBS during the 1994-1995 season.

Cherry also co-created The Crew (1995). On his own, he later created Some of My Best Friends, a 2001 sitcom that was based in part on the film Kiss Me, Guido.

In 2002, a conversation with his mother inspired him to develop a show about the fractured lives of four upper middle class suburban women. After HBO, FOX, CBS, NBC, Showtime, and Lifetime Television all passed on the show, Cherry got his big break when his agent was arrested and sent to jail for embezzlement. His new agents brought the show to ABC, which decided to pick it up. The series, Desperate Housewives, was an immediate ratings smash and generated enormous national (and subsequently, international) debate. Cherry received several lucrative offers from various parties, but chose to sign a long-term deal with Touchstone, since their network had shown faith in Desperate Housewives when no one else would.

The show was a phenomenon for much of its first season, but was criticized by TV critics who said the second season of Desperate Housewives was not as creative or as good as the first. Viewers seemed to agree, since the ratings dropped as the season progressed. Cherry, the Head Writer, who had been working part-time on the show in season two, took a larger role in developing and producing season three.

Cherry has featured several actors on "Housewives" that he has worked with before; Mark Moses, who played Paul Young, and Harriet Sansom Harris, who played Felicia Tilman, were both cast members of The 5 Mrs. Buchanans. In season three, Cherry cast former boss Dixie Carter in the role of Gloria Hodge, Orson's unhinged mother. Actor Alec Mapa, who appeared in Some of My Best Friends, appears on "Housewives" in a recurring role as Gabrielle's stylist.

On April 5, 2010, former Desperate Housewives cast member Nicollette Sheridan filed a 20 million dollar lawsuit against Cherry and ABC, alleging that he had assaulted her on set and wrongfully terminated her contract. Sheridan also alleged in her lawsuit that Cherry was abusive to other actors and writers on the show. ABC said in a statement that they had investigated similar claims made by Sheridan and found them to be of no merit.

Cherry appeared as himself in an episode of Arrested Development, which was created by fellow Golden Girls writer Mitchell Hurwitz.

Cherry was described in an article about him in Newsweek as a "somewhat conservative, gay Republican."