Artists whose most popular song came well after their initial rise to fame

what about Édith Piaf and Non, je ne regrette rien?. Not recorded until nearly the end of her life

I think some of this has to do with changes in the way charts were tabulated (though also his incredibly long run as a popular artist) and the emergence/timing of Youtube but I would imagine something like “Eat it,” “Fat,” or perhaps “Amish Paradise” at the latest would be his most popular. Or am I wrong and “White and Nerdy” really surpassed all that?

I disagree. You might justifiably argue that a different song is an artist’s best song or signature song. But an artist’s most popular song is the one that sells the most. And Billboard placement is based on sales.

Okay, maybe there’s a variation from year to year so a the #2 song in one year might sell more copies than a #1 song in a different year. Or maybe a song might linger on the charts for years, cumulatively selling a lot of copies without ever hitting the #1 spot. But I don’t think either of these circumstances is common. If you’re talking about an exception where a song with a lower chart position sold more copies, you need to back it up the evidence.

I disagree. One problem is with chart toppers, that’s only a snippet of time, not career. An artists most popular song over the span of their career may not be the highest charting one. I sincerely doubt anyone could seriously consider “My Ding-a-Ling” to be Chuck Berry’s most popular song. Highest charting? Yes. Most popular? Not by what I would consider a more reasonable definition.

Murray Head’s biggest hit was One Night In Bangkok. Released 14 years after Superstar.

I’m not sure why you’re disagreeing with something I clearly framed as an opinion, but okay. Keeping with the Elton John example, have you ever heard of a song called “Island Girl”? Not unless you’re a true fan would be my guess, or maybe heard it in passing if you own the Rock of the Westies album, but I doubt you’ve even heard of that (not a personal slight, just saying it’s not a well-known album of his). And yet it reached number 1 and stayed there for 15 weeks!

Now, have you ever heard of “Your Song”? You know, “I hope you don’t mind, I hope you don’t mind…”. Of course you have. You can’t escape it. Peak chart position? 8.

All I’m saying is there are many, many reasons why a more “popular” song might not have placed as highly on the charts. Maybe the higher song didn’t age well and nobody born after a certain year has heard of it. Maybe the lower song was used in a movie and blew up years later. The charts are useful, but they’re not gospel.

It’s based partially on sales of singles and partially on radio airplay, although the policies have changed over the years (Wikipedia). Album sales are not factored in, and as Wikipedia notes, in the '90s it became fairly common for record labels to not release singles commercially in order to boost CD sales. Until 1999 songs not commercially released as singles were not included in the Billboard charts, so there are popular songs of the era (e.g. No Doubt’s “Don’t Speak”) that were heavily played on the radio/MTV and helped push the album up the charts but never made the singles charts.

There are a few others that were released commercially as singles well after they were radio/MTV hits, and so did eventually make the Hot 100 but at a much lower position than if they’d been eligible when they were getting the most airplay. For example, in 1992-93 Pearl Jam’s “Jeremy” made it to #5 on the Billboard Mainstream Rock and Modern Rock charts based on radio airplay, but wasn’t eligible for the US Hot 100. (It was released commercially as a single in other countries and charted in several of them.) The international single was re-released in the US in 1995 and reached #79 on the Hot 100.

If we take Billboard Hot 100 position as the sole measure of popularity then Pearl Jam qualifies for the OP, as their highest charting single was “Last Kiss” in 1999 (#2). That’s much, much better than “Jeremy” did on the Hot 100. However, “Last Kiss” was released after Billboard changed the rules on radio airplay that had originally kept “Jeremy” off the charts. Both singles were certified Gold (500,000 copies sold). But Pearl Jam’s debut album Ten, which included “Jeremy” and was the only way to buy “Jeremy” in the US for several years, sold 13+ million copies in the US.

I actually think it’s fairly common. Since I’ve got the Wikipedia entry on Pearl Jam’s discography open, I can tell you that their second highest-charting single and only one aside from “Last Kiss” to make the top ten was “I Got Id” in 1995 (#7). It apparently failed to go Gold though, and so sold less than 500,000 copies. Their biggest-selling single of all time and also their only single to go Platinum (1 million copies sold) was 2009’s “Just Breath”…which peaked at #78.

Among her non regrets is her international hit from 14 years earlier, La Vie en rose. Looking at her list of songs, one could possibly find other popular ones. Per Judith Thurman in 2007, La Vie en rose was inducted into the Grammy Hall of Fame in 1998.