Michael McDonald is one of the most celebrated singer-songwriters of the 20th century and beyond. The five-time Grammy winner has been a member of Steely Dan and The Doobie Brothers and has collaborated with a wide variety of bands and artists including Kenny Loggins, Patti LaBelle, Van Halen, Toto, Ray Charles, Aretha Franklin, Thundercat and many more. McDonald has also had a successful solo career, releasing eight albums since his 1982 solo debut If That’s What It Takes. But having such a wide-ranging body of work, there are many aspects of McDonald’s career that you might not be aware of. Here are five things you didn’t know about Michael McDonald.

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1. Discovery

Michael McDonald grew up in the St. Louis suburb of Ferguson, Missouri. While in high school, McDonald played in a number of local bands including Mike and the Majestics, Jerry Jay and the Sheratons, the Reebtoors and The Guild. McDonald was discovered while playing in a band called Blue. When he was just 18 he moved to Los Angeles to pursue a music career, which he certainly found.

2. Film

After an extremely successful stint with The Doobie Brothers, McDonald began his solo career in 1982. In 1986 his Grammy-nominated single “Sweet Freedom” was featured on the soundtrack to the Billy Crystal, Gregory Hines movie “Running Scared.” McDonald also helped South Park’s Trey Parker record the song “Eyes of a Child” for the film “South Park: Bigger, Longer & Uncut.”

Although he did not appear in the movie in person, McDonald has a memorable reference (see above) in the 2005 comedy, “The 40-Year-Old Virgin.” Jane Lynch’s character—who plays the boss at the electronics store where Steve Carell’s character works—keeps a Michael McDonald live concert on repeat on the big screen televisions in the store, driving her employees nuts. As we shall see in the next section, Michael McDonald has always been good-natured about poking fun at himself.

3. Television

Michael McDonald has one of the most distinct voices in rock, and that being the case, he has been the subject of some hilarious parody, some of which McDonald himself has participated in. In 2013, McDonald appeared with Jimmy Fallon and Justin Timberlake on “The Tonight Show.” The trio sang “Row Row Row Your Boat” with Fallon and Timberlake wearing white whigs and impersonating McDonald’s vocal style. The singer has also been parodied in a number of Seth MacFarlane’s animated projects. On the “Family Guy” episode “Padre de Familia,” Peter Griffin enlists McDonald as his own personal backup singer. McDonald voices himself as Cleveland Brown’s neighbor on “The Cleveland Show” episodes “Skip Day” and “Mama Drama.” McDonald has also appeared on “30 Rock” and “American Idol.”

4. Regulate

In 1994, rapper and DJ Warren G sampled McDonald’s 1982 Grammy-nominated hit “I Keep Forgettin’ (Every Time You’re Near)” on he and Nate Dogg’s hip-hop classic “Regulate.” The hip-hop track features McDonald’s distinctive Fender Rhodes electric piano line. You can check out the original above.

5. Record Label

In 2000, McDonald teamed up with studio whiz Chris Pelonis and actor Jeff Bridges to found the independent record label Ramp Records. Both McDonald and Bridges have released albums on the label. Here’s what McDonald had to say about the venture. "This label, and many like it, are the result of so many artists feeling the need for this industry to re-invent itself. Not unlike FM radio in the sixties, the internet could become the free airwave of this generation, and the new small independent labels could just be responsible for bringing the same kind of unique, organic talent to the public’s attention that labels like Sun, Scepter, Chess and Stax-Volt were able to do."