Pitchford was born in Honolulu, where he attended Catholic schools, graduating in 1968 from Saint Louis High School. He began his performance career as an actor and a singer with the Honolulu Community Theatre (now Diamond Head Theatre), the Honolulu Symphony Orchestra and the Honolulu Theatre for Youth, among others. While studying at Yale University, Pitchford performed with numerous campus drama groups, but his focus gradually turned off-campus, where he worked with the Wooster Square Revival, an experimental theatre company that offered acting opportunities to recovering addicts and alcoholics. In 1969, Pitchford returned to Honolulu as an assistant to authors Faye Hammel and Sylvan Levey in updating the popular guidebook Hawai'i on $5 and $10 A Day, and researching Trans World Airlines' Budget Guide to Hawai'i, the first of a series of guidebooks that would eventually turn into the popular series TWA Getaway Guides.

Inspired by a 1979 news story about Elmore City, Oklahoma, a town which had finally lifted an 80-year-old ban on dancing, Pitchford wrote the screenplay for the motion picture Footloose (1984). He collaborated on the nine-song score with Kenny Loggins, Eric Carmen, Jim Steinman, Sammy Hagar and others. The film, directed by Herbert Ross, opened at #1 and was, at the time, the highest-grossing February release in film history.  When the soundtrack album hit #1 on the Billboard album charts, it deposed Michael Jackson's Thriller and held that position for 10 weeks. It went on top charts all over the world, eventually selling more than 17 million albums. Kenny Loggins's single of the title song hit #1 on March 31, 1984, and stayed there for three weeks. Five weeks later (May 26, 1984) Deniece Williams's "Let's Hear It for the Boy" went to #1, as well. Four more songs from the soundtrack charted in the Top 40; "Almost Paradise," which reached #7, was co-written with Eric Carmen, and was performed by Mike Reno of Loverboy and Ann Wilson of Heart; "Dancing in the Sheets," which reached #17, was co-written with Bill Wolfer, and was performed by Shalamar; "I'm Free (Heaven Helps the Man)," which reached #22 and, like the film's title track, was co-written with, and performed by, Kenny Loggins; and "Holding Out for a Hero," which reached #34, was co-written with Jim Steinman, and was performed by Bonnie Tyler. "Footloose" was nominated for a Golden Globe as Best Song; and "Footloose" and "Let's Hear It for the Boy" (co-written with Tom Snow) both received Academy Awards nominations (1985). Pitchford received two Grammy nominations: Best Soundtrack Album for a Motion Picture, Television or Other Visual Media, and Best R&B Song "Dancing in the Sheets."  Paramount Pictures's remake of Footloose, which was again based on Pitchford's original screenplay and featured six of his songs, was released in October 2011. Blake Shelton had a hit with his re-recording of the title song.  Next Pitchford wrote the screenplay of, and collaborated on the authorship and composition of all the songs for, the 1989 musical film Sing.

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