Prior to Santana, he played with a group called William Penn and His Pals while attending Cubberley High School in Palo Alto, California 1965, his senior year.

As a co-founding member of Santana, Rolie was part of the band's first wave of success, including an appearance at the Woodstock Music and Art Festival in 1969[2] and central roles in several hit albums.

He was their original lead vocalist, with his voice appearing on well-known Santana songs such as "Black Magic Woman" (US #4), "Oye Como Va", "No One To Depend On" and "Evil Ways".

After Steve Perry joined the band in 1977, Rolie sang co-lead vocals on several songs on the albums Infinity, Evolution, and Departure.

This album featured the song "I Wanna Go Back", which later became a hit for Eddie Money, and included contributions from Carlos Santana, Peter Wolf, Neal Schon, and Craig Chaquico.

Besides Rolie and Wikso, Roots featured appearances by Neal Schon, Alphonso Johnson, Dave Amato, Adrian Areas and Michael Carabello.

[6] The band also included Toto guitarist Steve Lukather, Todd Rundgren, Richard Page, Mark Rivera and Gregg Bissonette.

[8] On February 9, 2018, Rolie reunited with Schon for a charity show at San Francisco's The Independent, benefiting North Bay Fire Relief.

The group also featured former Journey drummer Deen Castronovo (who also sang some of the vocals) and bassist Marco Mendoza of The Dead Daisies.

In 2005, he signed on as an official supporter of Little Kids Rock, a nonprofit organization that provides free musical instruments and instruction to children in underserved public schools throughout the US.