My Musical Heroes Who Have the Most Enviable Career
To Me, At Least
Posted by Charlie Recksieck
on 2026-11-03
A few times I've been asked if I could have anybody's musical career, who would I choose?
It's an interesting question.
I honestly wouldn't have wanted to be too huge where I would have to have an insulated life like Paul McCartney or Bruce Springsteen, as much as I love their catalogs.
Being a pure rockstar like Prince, Axl Rose or Mick Jagger doesn't appeal to me.
When answering the question, I try to picture actually living that person's life. As much as I love their music, I wouldn't want to spend my life constantly touring like Billy Joel and Willie Nelson, reportedly due in part to bad money decisions, or make the not-quite-superstar money of Lucinda Williams or Ben Folds.
I think I've come up with a few here who would be my perfect career ideal in some fantasy life.
I'll warn you now; 4 of these 6 dudes are piano players.
Another trend: most of them started a family, stayed married and had a real life - not a Mick Jagger / Jerri Hall situation.
Elvis Costello
He's usually my default answer to this question.
For starters, he wrote some incredibly critically acclaimed albums like Armed Forces and Trust right out of the gate, and several of his that carry a lesser reputation like Mighty Like A Rose and Goodbye Cruel World are favorites of mine.
An intellectual rock star.
He got to live the wild touring life while young, without having to sustain that forever.
He got to experiment with different musical styles and collaborators, even if some experiments (string quartets, ahem) aren’t necessarily my bag.
Collaborated with Burt Bacharach and Paul McCartney; I would list more partners but what's the point after those two.
Elvis dabbled in funny acting roles that were a little more than cameos.
Austin Powers: The Spy Who Shagged Me is probably his best known, the Jean Girard garden-party scene in Talladega Nights is the greatest wow appearance - but then I was a fan for life from multiple appearances on The Larry Sanders Show, possibly the greatest television show of all time (yeah, I said it), where he's a major plot point in two episodes.
The classic-car sale to Hank that turns out to be a lemon is an alltimer.
He built a family and has a personal life alongside the career.
And then more recently, he wrote Unfaithful Music & Disappearing Ink, a terrific book about music and life - which includes his memorable argument about how guitar students are made to learn C and F chords too early.
Bruce Hornsby
Some casual fans might think of him just as the "The Way It Is" guy, but he’s continued to make adventurous music for decades.
I love his catalog, songwriting, lyrics, and piano chops so much that I'm not going to go down that rabbit hole right now.
He’s also been sweet enough to leave me two very considerate voicemails - and the only reason I’ve ever regretted not answering a call from an unknown number.
He had huge success in the late 1980s, but didn’t get stuck trying to recreate it.
Then once he assembled The Noisemakers, he found my perfect band.
Their size of venues seems just right: a devoted audience, great musicianship, and no need to be a stadium superstar.
Oh hold on, he was a member of the goddamn Grateful Dead in the early 1990s.
He wins.
He also had so many incredible collaborators.
Made "I Can’t Make You Love Me" with Bonnie Raitt, wrote all of the music for "The End of the Innocence", recorded it and sent it to Don Henley to finish up and make into a hit, and co-wrote "Go Back to Your Woods" with Robbie Robertson.
Bruce collaborated with an extraordinary range of artists, from Ricky Skaggs to Bon Iver.
He worked extensively with Spike Lee on film music, including Clockers, Get on the Bus, and Bamboozled. Hornsby is free to delve into complex modern classical music, like the work of Ligeti, or jam with Bela Fleck or the Dead.
He may have been sampled in more hip-hop songs than anybody.
He can tour solo when he wants a different kind of performance and touring experience.
If that all wasn't enough, Bruce is a sports freak.
He's a legit good basketball player and wrote a few incredible songs about hoops, including my favorite "Rainbow's Cadillac."
Hornsby has joked that he used to tour just so he could get great seats and sideline tickets to major sporting events.
He has a family and two sons who played Division I college sports.
Paul Shaffer
Is he a songwriting legend like the rest of these guys?
No, but he did co-write "It's Raining Men."
There are some truly funny piano players on this list (Tom Waits, Randy Newman) but Paul Shaffer's career completely straddled comedy and music.
On Letterman, his band backed an astonishing variety of musical guests, playing every genre and sitting in with artists like Miles Davis or Eddie Van Halen just about every night.
He was the founding musical director and keyboardist for the Blues Brothers.
His role as the Rock & Roll Hall of Fame’s house band and musical programmer gave him another opportunity to perform with music legends.
He became a cast member on Saturday Night Live, not just a musician. He was the perfect fit for David Letterman - and stayed with him on the air for over 30 years.
Paul was truly great in sketch work with Dave, or saving a bad segment.
Shaffer got to live the dream: to play music, perform comedy, interact with celebrities, and participate in memorable TV bits - all as part of a regular job.
Unlike a touring musician, he didn’t have to spend most of the year on the road to make a living.
He lived full-time in New York City, got married, raised a family, and maintained a relatively stable home life while working in entertainment.
Now here's the part that makes me the most jealous: He seems to be friends with everybody in entertainment, and even closer with the funniest people, such as longtime friendships with Martin Short, Christopher Guest, Gilbert Gottfried and other comedy-world luminaries.
If there's one place I'd want to be in entertainment, it would be at a Wayne Newton show with Martin Short and Eugene Levy - or as a guest at one of Paul Shaffer's annual "celebrity seders."
Robbie Robertson
I mentioned earlier that Elvis Costello got to sow his wild oats in his early career but that's nothing compared to Robbie Robertson.
At 15 he hit the road with Ronnie Hawkins' band getting a musical education onstage and a sexual education on the road.
Then Robertson got the ride of a lifetime with what would become The Band being Bob Dylan's band when he went electric, and holed up at the Big Pink house in Woodstock making the Basement Tapes.
From there, he put some of the best rock music and albums of all time with The Band.
Robertson wrote maybe 8 or 9 of my favorite 100 songs of all time, not just the ones on The Band, or Music From Big Pink.
When the band (The Band) fell apart, his new collaborator became Martin Scorsese - although they also collaborated on a LOT of cocaine. I loved his next job: music coordinator for films, usually for Scorsese, where he picked the best soundtrack and score music based on his knowledge of film and music.
That might be my dream job more than professional musician.
Then in what is allegedly the quiet part of his career, Robertson made two of my favorite albums, his 1987 eponymous one and the 1991 beauty Storyville. He still recorded later when he felt like it, but never had to tour to pay the bills.
Tom Waits
I'm seeing a trend here: early legendary songwriting at the same time they're indulging themselves with sex, drugs and rock n' roll.
Don't let Tom Waits' troubadour style fool you - he partied as well as anybody in the 1970s and had a legendary relationship with Rickie Lee Jones.
He's been an incredible songwriter and performer from the beginning, with a gift for storytelling that extends to his between-song patter. Listen to the 1975 live recordings and Glitter and Doom to appreciate just how funny he is.
As great as his early vagabond/raconteur/balladeer stuff was, a few years later he wrote some of the most unique landmark albums of all time. Swordfishtrombones (1983), Rain Dogs (1985), and Frank’s Wild Years (1987): one of the great runs of albums in music. Waits created his own musical universe with ballads, circus music, and made avant garde into pop.
Tom met Kathleen Brennan, who became his wife and essential creative collaborator.
Their partnership not only helped shape his later career, but he met the love of his life and raised three children.
He could sit alone at a piano and deliver a compelling performance without needing a band; but when he had one, like on the live Glitter And Doom record, it made his studio experiments into grand stage music.
Waits cultivated a strange public persona, but by all accounts he was a sweetheart.
He had a terrific rapport with Letterman, whose appreciation of Waits’ eccentricity made for memorable TV.
Waits' odd charisma led to legit great acting roles in things like Mystery Train (and two other Jim Jarmusch movies), Short Cuts, three Coppola pictures (The Outsiders, Rumble Fish, and Bram Stoker’s Dracula), The Ballad of Buster Scruggs with the Coen Brothers.
And then there are the theater projects and collaborations with the likes of director Robert Wilson and writer William S. Burroughs.
Overall, Tom got to live the pure artist’s life, with a lasting marriage and family.
That's about as good as show business gets.
Randy Newman
He was my piano-playing model as a teenager. His phrasing, left hand, New Orleans piano vibe, and ability to accompany himself were things I wanted to do.
I have been described in a review as "the stupid man's Randy Newman" which is my favorite pull quote for my music.
Randy was a hilarious and/or poignant songwriter who can write about virtually any subject, no matter how unusual.
His own catalog includes classics like Sail Away, Good Old Boys, and 12 Songs.
Newman had surprise hits with "Short People" and "You’ve Got a Friend in Me," neither of which comes close to representing the full depth of his work.
His day job - and a career I would absolutely love - is composing film scores. A short list of some of the best film music would have to include The Natural, Tucker, Avalon, and Ragtime, all of which was his. Tack on Parenthood, Toy Story, Seabiscuit, Meet the Parents, and Marriage Story, among many others, and you start to get the picture.
Newman is totally fully realized as a solo act, playing piano and singing his songs at good venues without needing a big band or production.
He has been able to attract legendary musicians to his records and projects any time he wants.
He's won two Academy Awards for Best Song and a huge run of nominations for Best Score.
Randy is a relaxed, funny motherfucker (at least the one time I was in the same room with him) who seems to have managed a remarkable career and big-hitter showbiz friends without becoming a celebrity.
His humor can be biting, absurd, and deeply uncomfortable in the best way.
Let's put it this way: Lorne Michaels reportedly called him "the funniest person I know" - which is an insane compliment from the guy who created and spent his whole career among comedy legends, running Saturday Night Live.
Randy Newman became an acclaimed songwriter, a terrific pianist, a successful film composer, and a musical-theater creator.
His day job of composing scores allowed him the freedom to write some of the most iconoclastic songs in rock history.
Randy had major commercial success without becoming a full-time pop star.
