Paul McCartney is an accomplished painter and has written several children’s books.
Deniz Tek - one of the founding members of Radio Birdman, 70’s pre-punk band from Sydney, and still actively performing. As his Wikipedia page exhaustingly describes:
Tek is a trained ER doctor and ex-navy flight surgeon who currently splits his time working in emergency departments in hospitals in New South Wales and Hawaii while still taking time to record and tour.
Caveat: I’ve never listened to The Mountain Goats so I’m not sure if they truly rock.
But one of the band’s members wrote a book called Devil House which I loved. It’s literary fiction blending true crime with journalism. There are parts of it that are downright experimental. He’s written three books.
While opinions on Devil House are mixed, he is a solid, skilled writer with a lot of depth. These aren’t vanity projects.
Greg Kihn of the Greg Kihn Band was a morning deejay and the author of several horror novels. I tried one and didn’t care for it, but it was nominated for a Bram Stoker award.
Trevor Hurst, lead singer of Canadian rock band “Econoline Crush” (and they kick ass in their music) became a nurse who has become a trusted member of a Canadian Indigenous community in Manitoba.
Here’s a CBC article about him:
https://www.cbc.ca/news/canada/manitoba/trevor-hurst-canupawakpa-dakota-nation-1.7111590
(emphasis added) excellent typo
I meant to do that!
After being lead guitarist with Country Joe and The Fish, Barry Melton had an impressive career as a lawyer.
And Tek, as a flight surgeon, was the original Iceman, although it seems the writers didn’t steal his call sign. I must admit I love the idea of a “call sign committee”.
He’s in his 70s and quite a bit older than me, but with that sort of lifestyle he makes me feel like Grandpa Simpson.
And for those who’ve never seen or heard Radio Birdman try this.
Guitarist, Steve Morse (Dixie Dregs, Kansas, Deep Purple) worked for a short time in the 80s as a commercial airline pilot.
Was. He’s recently stopped due to regulations and his age. But it was glorious to to see Ed Force 1 land at LAX with Bruce at the helm!
Maynard James Keenan, the singer for Tool, A Perfect Circle, and Puscifier, owns a vineyard and has his own wine label.
I was going to mention Steve Morse. If I remember correctly he got disillusioned by the industry. He put in a lot of work and got tons of critical acclaim but it didn’t translate to album sales.
To me he’s the best guitar player ever. I first saw him live back on the first Steve Morse Band tour. It was at The Stone Pony and I stood 5 feet away and was mesmerized. Didn’t see him live again until he was with Flying Colors, a woefully underrated band. I saw each one of their 3 live tours. In recent years I saw the reunion tour of the Dixie Dregs and the recent semi-tour of the Steve Morse Band.
He was the longest serving guitar player in Deep Purple but they wouldn’t let him be inducted with the rest of the band into the Rock and Roll Hall of Fame. Which is bullshit. He left Deep Purple a few years ago when his wife got very ill. That’s when he started doing sporadic dates with his trio. He couldn’t do a prolonged tour. Sadly she died last year.
Jon Bon Jovi has a couple of restaurants. At JBJ Soul Kitchen you can go eat and pay a suggested donation. Or if you are in need you can eat for free. Or you can volunteer to work there. It’s an interesting concept and execution.
J. Geils owned an auto repair shop that specialized in vintage Ferraris.
Captain Beefheart aka Don Van Vliet also was a respected and successful painter.
ETA: painting seems to be a frequent side hustle for singers. Bob Dylan, Joni Mitchell and Ron Wood also come to mind. And both Graham Nash and Bryan Adams are serious photographers.
ETA2: Pete Townshend was an editor for Faber&Faber in the 80s. He also, like Dylan, is an author.
Has anyone mentioned Jack White of the White Stripes? He apprenticed as an upholsterer before hitting it big in music, had his own shop, and still does it as a hobby.
Gerard Way, lead singer of My Chemical Romance, also writes comic books. You may have heard of at least one of them (or at least the TV series based off it) - The Umbrella Academy.
Probably more ‘retirement hustle’ than ‘side hustle’, but former Rolling Stone Bill Wyman, an avid detectorist, designed and sold a signature metal detector.