He is best known by most for his Top Ten hit songs, "Sailing", "Ride Like the Wind", and "Arthur's Theme (Best That You Can Do)," the latter of which he performed for the film Arthur starring Dudley Moore and Liza Minnelli. "Sailing" earned three awards at the 1981 Grammy Awards Ceremony, while "Arthur's Theme" won the Oscar for Best Original Song in 1981 (with co-composers Burt Bacharach, Carole Bayer Sager and Peter Allen.)

Cross first played with a San Antonio based cover band named Flash before signing a solo contract with Warner Bros. Cross released his self-titled debut album, Christopher Cross in 1979, which garnered him five Grammy Awards. He is the first and only artist to personally receive all of the "Big Four" Grammy Awards (Best Record, Song, Album, and New Artist) in the same year. Hits from this album included "Sailing", "Ride Like the Wind" (featuring backing vocals by Michael McDonald) and "Never Be the Same".

His second album, Another Page, which came out in 1983, included the hit songs "Think of Laura", "No Time For Talk", and "All Right." "All Right" was used by CBS Sports for its highlights montage following the 1983 NCAA Men's Division I Basketball Tournament, won in an upset by North Carolina State, which defeated the University of Houston in the championship game, 54-52. Although Another Page sold respectably, it did not nearly live up to the high expectations set by his debut album.

Cross released his third album Every Turn of the World in 1985. However, the album failed to produce any top 40 hits, and did not sell well. He went on to make three more albums in the 90's and although some of his releases have gained critical response, he has failed to catch the mass audience he once enjoyed. After his decline in fame in the mid-1980s, Cross has toured and opened for various acts since the 90's and releasing his second Greatest Hits package in 2002.

Cross completed a new Christmas album and on November 15, 2007, which was released exclusively on iTunes and is slated to be in general distribution for the 2008 season. Christopher has just finished recording a new acoustic album of his hits titled "The Carlye Sessions". He is also working on a new studio album that is expected to be released in the spring of 2009. Today, he does about 100 live performances a year.

In recent years, his daughter, Madison has become a singer and actress.