At the dawn of the 1980’s, there was virtually no bigger name in popular music than Rick James. In honor of James’s birthday today, we remember the singer-songwriter-guitarist-showman via his most enduring musical works and his most notable periods of cultural influence.

James burst onto the scene in 1978 with the release of his debut album Come Get It! via Motown offshoot Gordy Records. The album would go on to sell more than two million copies, but it was his 1981 album Street Songs (featuring hits like “Give It To Me Baby” and “Super Freak”) that catapulted James—and his sexual-yet-silly brand of funk—into the global consciousness. Below, you can watch James’ put on a show in the music videos for “Super Freak” (Come Get It!, 1981) and “Hard To Get” (Throwin’ Down, 1982), respectively, courtesy of RickJamesVEVO:

While his music remained successful, James’ reckless lifestyle gradually ran his career off the tracks. He continued to write and collaborate on new music with various artists throughout the 80’s and 90’s (including Eddie MurphySmokey Robinson, and The Temptations), but his solo career fell off considerably as his lifelong drug addiction problems worsened. To make matters worse, he received a three-year prison sentence after being convicted of kidnapping and torturing two women under the influence of crack cocaine.

In 2004, after years out of the spotlight, James once again became a cultural icon with the help of Dave Chappelle and Chappelle’s Show. In perhaps the most famous comedy sketch on the most famous sketch comedy show of all time, “Charlie Murphy’s True Hollywood Stories”, Chappelle’s Show writer Charlie Murphy tells a series of stories about his precarious experiences partying with James in his coke-fueled heyday. In the sketch, Murphy’s telling of the stories is interspersed with commentary by Rick himself, as well as full dramatizations of the action starring Chappelle as James. The episode has remained a frequently quoted relic of the fantastic Chappelle’s Show long after the show went off the air in 2005. You can watch parts 1 and 2 of Charlie Murphy and Dave Chappelle’s Rick James saga below, courtesy of Comedy Central:

Later that year, James succumbed to a life of drug and alcohol abuse, passing away at the age of 56 from heart failure. James’ legacy is undoubtedly a mixed bag, but his infectiously catchy music and hilarious rendering on Chappelle’s Show ensured that he is one star the world won’t soon forget.