(March 20, 2023).  Gilbert O’Sullivan, 76-year-old singer/songwriter who shot to stardom in the early 1970s with a string of top-40 pop hits that began with one of the biggest singles of the decade’s first half, performed a two-hour show at Chi’s City Winery on Sunday (March 19).

With just an accompanying guitarist, a Roland keyboard, a songbook, a microphone and his strikingly full curly afro in tow, the “Get Down” singer rolled through a setlist that included 28 songs (four of which reached the top 40 here in the U.S.—he sadly omitted his last American top-40 hit, “Ooh Baby”), some interesting stories about the tunes’ origins, and a few anecdotes to keep the small crowd of about 200 fully entertained.

And that’s exactly what the affable singer originally from Waterford, Ireland did—and surprisingly, none of his jokes had anything to do with the weekend’s St. Patrick’s Day holiday that some of us fully expected the Irish hitmaker to leverage in a nod to his homeland.

Instead, we heard stories about his reluctance to sing duets (and the only four artists he’s ever done that with in his 50-plus year career), his thoughts on the violence in Ukraine (and the song he dedicated to the beleaguered nation), plus remembrances of past touring experiences that were simultaneously self-effacing and self-affirming.

Singer/songwriter Gilbert O’Sullivan is still making great music. He released the Driven album in 2022

For example, before playing a beautiful ballad called “Happiness Is Me and You” (accompanied only by the acoustic guitar of that lone accompanying musician Bill Shanley), O’Sullivan recalled an earlier concert where two women in attendance were discussing whether or not the singer they were observing was the real deal.

Said one woman to the other about O’Sullivan, as Gilbert recalled it, “I think he’s a tribute artist.”  “Why?” asked the other woman in response.

“Because he’s too young to be the original singer.”  

That punchline elicited both laughter from Sunday night’s crowd and a few under-their-breath acknowledgments from people in the audience that O’Sullivan indeed looked younger than his 76 years, owed in part to that very healthy afro he was sporting.

It’s those 76 years that allowed O’Sullivan to be forgiven for some very generous math he used when recalling the well-documented but oft-misquoted (by fans) story of his inspiration behind the 1972 tune “Clair,” his second-biggest hit here in the States.  

He reminded us that the song had been inspired by his then-manager’s very young daughter, who O’Sullivan would often babysit while he was an up-and-coming artist.  He confirmed that it was indeed Clair’s chuckle you hear at the end of the record, which rose to No. 2 on the Billboard Hot 100 in December 1972.  

But it was the story’s payoff that sent mental calculators into overload: “Clair is now 40-something with her own kids.”

While Clair—if she ever gets wind of her famous former babysitter shaving a few years off her age—would likely appreciate his generosity when describing the song she inspired, we in the audience were very appreciative of his generous song set, which  included familiar oldies like “Clair” and “Out of the Question,” plus some new songs (his most recent album, the appropriately titled Driven, came out in 2022).

From that album, O’Sullivan performed the only two duets he’s recorded since earlier in his career (when he only performed two others).  The first was the peace-seeking song “Let Bygones Be Bygones” featuring Mick Hucknall of the group Simply Red.

The other was the very upbeat (and uplifting) “Take Love,” sung on the album with Scottish singer K.T. Tunstall (of “Suddenly I See” fame), who—as with Hucknall—was not present Sunday night.

It was during the lead-up to “Bygones” that the audience learned of two of O’Sullivan’s biggest musical inspirations—the late 20th century legends Peggy Lee and Ella Fitzgerald—whom the ‘70s hitmaker referred to as the best song interpreters (with Lee being one of Gilbert’s two earlier duet partners).

Another track from the new album, “Blue Anchor Bay,” was described by O’Sullivan as one of the few he’s written that was based on a real life experience (this is where he inserted the story of “Clair” as being another rare example).  

This news was somewhat comforting to those of us who’d dissected the lyrics to his biggest, but most depressing hit, “Alone Again (Naturally),” a song he took to No. 1 for six weeks in 1972, making it one of the biggest hits of the 1970s.  That sad tune told (in first-person) of suicidal thoughts following the indescribable loneliness associated with the protagonist being left at the alter, and the heartbreaking loss of both his parents. 

Who among us didn’t shed tears upon first hearing “Alone Again (Naturally)” during our youths?

That song was obviously a key part in Sunday’s 28-song setlist, which had other poignant moments, including the biggest audience participation segment where the singer spoke of his displeasure surrounding the events in Ukraine before leading the engaged crowd into a chorus of “Where Peaceful Waters Flow” (from his 1973 album I’m a Writer, Not a Fighter).

Another nostalgia trigger was the ballad “Dansette Dreams and 45s,” a tune where, in the lead-in, the veteran singer felt the need to explain to this crowd of mostly fifty-somethings and older what a “45” was.  

More appreciated was his explanation of the term “Dansette,” which as it turns out was a long-ago British manufacturer of record players (on which O’Sullivan played those 45s), which stopped production in the late 1960s (I had to look that last part up).

On another ballad, the song “Lost a Friend,” Gilbert told how the song had been inspired by the deaths of Elvis Presley and John Lennon, while recalling the huge impacts of those losses on him and others.

Otherwise, the show also had its uptempo moments, which at one point had people clapping, singing and even dancing along in a couple notable cases.

The most upbeat of those tunes were “Came To See Me Yesterday,” “I Don’t Love You But I Think I Like You,” “No Head For Figures But Yours,” “Matrimony,” and the show’s closer, “Get Down.”

Gilbert O’Sullivan performs “Get Down” at City Winery Chicago on Sunday, March 19, 2023

By the time “Get Down” played, I was reminded of a comment overheard at a table nearby from another attendee: “‘Get Down’ was the first 45 (he’d) ever bought.”

With that, and judging by the crowd’s very positive response to Mr. O’Sullivan, it was clear those “Dansette Dreams” were still alive and well in many of the folks at this night’s show.

I recommend seeing Gilbert O’Sullivan to anyone with an early ‘70s nostalgic bug who wants to relive those memories and hear straight from the singer’s mouth how some of his most popular hits came to be…plus some pretty good new stuff as well!

Here’s Gilbert O’Sullivan’s set list from Sunday night (March 19, 2023):

  1. The Same the Whole World Over
  2. A Friend of Mine
  3. Came to See Me Yesterday
  4. Nothing Rhymed
  5. Let Bygones be Bygones
  6. Miss My Love Today
  7. All They Wanted to Say
  8. We Will
  9. Take Love
  10. Dansette Dreams and 45s
  11. Where Peaceful Waters Flow
  12. Ooh Wakka Doo Wakka Day
  13. Claire (end of first set)
  14. At the Very Mention of Your Name
  15. No Matter How I Try
  16. Lost a Friend
  17. No Way
  18. Blue Anchor Bay
  19. I Don’t Love You but I Think I Like You
  20. Happiness Is Me and You
  21. Why, Oh Why, Oh Why
  22. No Head for Figures but Yours
  23. If I Don’t Get You (Back Again)
  24. Out of the Question
  25. What’s In a Kiss 
  26. Alone Again (Naturally) (end of second set)
  27. Matrimony (encore)
  28. Get Down


Fellow Dansette dreamer DJRob (he/him/his) is a freelance music blogger from somewhere on the East Coast who covers R&B, hip-hop, pop and rock genres – plus lots of music news and current stuff!  You can follow him on Twitter at @djrobblog.

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By DJ Rob

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