In 1985, Drayton contributed percussion work on the Rolling Stones' album Dirty Work, which led Keith Richards to ask him to become a founding member of his side projectX-pensive Winos in 1987. As bassist, Drayton toured and recorded with Richards and the Winos until December 1992, and played on their albums Talk Is Cheap and Main Offender, and the live album and video Live at the Hollywood Palladium, December 15, 1988. Richards describes Drayton as one of his all-time favorite drummers. Drayton played drums on four tracks of The B-52's 1989 album Cosmic Thing, including the singles "Channel Z" and "Love Shack". However, Zack Alford, who subsequently toured with the group on drums, appeared in the videos for both songs. Drayton played bass guitar alongside Neil Young on the September 30, 1989 Saturday Night Live performance of "Rockin' in the Free World" He played bass guitar on The Cult's 1991 album Ceremony. He played drums on two albums for Australian band Divinyls: 1991's Divinyls and 1996's Underworld, the band's last album before their hiatus in late 1996. In 1999, Drayton married Divinyls' lead singer Chrissy Amphlett and the couple lived in New York City. In 2007, Divinyls reformed and Drayton played drums in their touring band and in their new recording sessions, also producing the band's new album. Amphlett died of complications from breast cancer and multiple sclerosis on April 21, 2013. In 2008 and 2009 he recorded and toured with Paul Simon. In 2010 he toured with Simon & Garfunkel. Paul Simon said "Charley's the heart of the band and I'm very grateful that I have him. He comes in prepared, real serious and he’s a delight. He’s an all around great musician and a fine, fine drummer." He has been recording and touring with Australian rock band Cold Chisel since 2011, following the death of original drummer Steve Prestwich Drayton co-produced and played various instruments on Fiona Apple's album The Idler Wheel..., released in June 2012. In 2015 he played drums on French chart topper Johnny Hallyday's album De L'Amour, as well as on the number two charting album by Japanese artist Kazuyoshi Saito. In 2017 Drayton was on a world wide tour playing drums with Little Steven & The Disciples of Soul. Drayton was one of the major critics of Divinyls guitarist Mark McEntee's plans to reform the group with a new singer, stating in an angry Facebook post that McEntee's actions were the "ultimate disrespect" toward Amphlett.