The B-52’s were formed when Wilson (who was born in Athens, Georgia), guitarist Ricky Wilson (her elder brother), keyboardist and backing vocalist Kate Pierson, drummer and percussionist Keith Strickland, and lead vocalist Fred Schneider played an impromptu musical jam session after sharing a tropical Flaming Volcano drink at a local Chinese restaurant. They later played their first concert in 1977 at a Valentine’s Day party for their friends. Cindy Wilson was the youngest member of the band.

On April 21, 1985, she married Keith Bennett, a successful advertiser who was a longtime friend of the band and Ricky’s guitar tech on tour. Ricky died later that year, leaving her devastated.

Wilson plays the bongos on live favorites like “Planet Claire”, “Mesopotamia”, “Pump” and “Party Out of Bounds” as well as other songs such as “6060-842” and “Big Bird”. She also has played acoustic guitar in The Cindy Wilson Band, made electric guitar contributions (with her brother Ricky) on the songs “There’s a Moon in the Sky (Called the Moon)” from the B-52’s first album, and played the guitar solo for “Nip It In the Bud” during the band’s 1982 Mesopotamia tour. She has stated that she was encouraged to play guitar by her brother, but experienced finger pain. Cindy briefly played a note or two on the keyboard during the band’s Whammy! tour version of Private Idaho and at Rock In Rio 1985. She also played an electronic drum kit on a commercial for the WE tv network.

Wilson took a sabbatical from the band in 1990 to concentrate on raising a family of three children, during which time the B-52’s recorded and released the album Good Stuff as a trio of Pierson, Schneider and Strickland. During the live tour to promote Good Stuff in 1992 and 1993, Julee Cruise sang as a replacement for Wilson.

Wilson rejoined the B-52’s in 1994. In 1998, she took part in recordings for two new songs to be included with the band’s hit singles on the album Time Capsule: Songs for a Future Generation. Wilson then took maternity leave in 1999 (being replaced on tour by Gail Ann Dorsey), later rejoining the band in 2001 for regular touring of their greatest hits.

The B-52’s completed the album Funplex in 2007, and it was released in March 2008. Wilson co-wrote every song on the album with the three other band members. In all, she has co-written much of the band’s catalog, including “Dance This Mess Around”, “Private Idaho” and all of the Cosmic Thing album, including hit singles “Love Shack” and “Roam”.

Cindy Wilson self-released an EP of new material, Sunrise, in September 2016. February 2017 saw the self-release of another EP of new material, Supernatural.

Her debut full-length solo album Change was released in December 2017 on the Kill Rock Stars label.