In the 1950's Pepper became one of the most acclaimed West Coast players. His key albums were Art Pepper Meets the Rhythm Section (1957), which was considered his masterpiece, recorded in one take with Miles Davis’s rhythm section (Red Garland, Paul Chambers, Philly Joe Jones); Surf Ride; and Art Pepper + Eleven (arranged by Marty Paich), a West Coast classic.
In the 1960's and early 70's, he faced multiple incarcerations due to heroin addiction, and only made sporadic appearances and recordings.
After getting clean and rebuilding his technique, Pepper experienced a powerful resurgence, with albums like The Trip, Straight Life, Living Legend, Winter Moon, and One September Afternoon. His autobiography “Straight Life” (co-written with his wife Laurie) is considered one of the greatest, rawest jazz memoirs ever written. This final period contains some of the most emotionally charged playing of his life.