[1] He initially gained notability as a member of Alice Cooper's band, contributing bass to his Constrictor (1986) and Raise Your Fist and Yell (1987) albums.

At age 16, Winger began studying classical music after hearing the works of composers such as Debussy, Ravel, and Stravinsky in ballet class.

[a] As a teenager, Winger played in a band named Blackwood Creek with his brothers Nate and Paul plus friend Peter Fletcher (formerly in Pigmy Love Circus).

In 2002 Winger moved to Nashville, Tennessee and began working on his fourth solo record, From the Moon to the Sun (2008), which he co-produced with Cenk Eroglu.

In September 2006, it was announced that Winger would be reformed, with the Pull era line-up, to record the band's fourth studio album, IV, and to go on tour[6] to support it.

Following the release of From the Moon to the Sun, Winger studied with Michael Kurek and composed a thirty-minute symphonic piece, "Ghosts", written for strings, piano and harp for a ballet commission.

Winger's composition "Blue Suede Shoes" from the album IV honored the service and sacrifice of United States armed forces and their families.

[18] He has participated and performed as head counselor in the Rock 'n' Roll Fantasy Camp with other musicians including Roger Daltrey, Steven Tyler, Todd Rundgren, Jack Blades, Kelly Keagy, Bruce Kulick, Bill Leverty, Steve Lukather, Duff McKagan, Mark Slaughter, Carmine Appice, and Rudy Sarzo.

He was featured in an episode of the American TV show Pawn Stars in May 2013 as helping the host, Rick Harrison, through Rock Fantasy Camp.