This question is prompted by Taylor Swift’s song “Tim McGraw.” Her debut single, it got all the way to number six on Billboard’s Country chart and for all I know may have had some crossover appeal on the Hot Hundred. And the title of the single refers to country singer Tim McGraw, who himself has had multiple number one Billboard country singles.
So to revive a trivia interest born from weekly doses of Kasey Kasem in the 70s: has any number one song contained the name of a number one artist in its title?
ABC’s “When Smokey Sings” was #1 in the Billboard’s Hot Dance Club Songs charts. It refers to Smokey Robinson, who had two #1 hits in the US R&B charts (and certainly several others with the Miracles, but I was too lazy to look that up).
Miley Cyrus has that piece of dreck “Party in the USA” in which she sings “…and the Jay-Z song was on”. She also says “. . .and a Britney song was on” but that doesn’t mention her last name.
Hmmm… Stevie Wonder’s #1 song “Sir Duke” was about Duke Ellington, but I don’t know if the Duke ever had anything that could be officially termed a #1 record.
“Amrican Pie,” a number one hit, ALLUDES to several artists with #1 hits, without naming them (Buddy Holly, Elvis).
It also mentions the Byrds and John Lennon, who both hit #1. But it mentions them subtly "Lennon sounds like “Lenin,” while the Byrds (who had a big hit with “8 Miles High”) could be just ordinary feathered creatures.
At the end of the #1 hit “Love Will Keep Us Together,” Toni Tennille sings “Sedaka is baaaack,” an allusion to Neil Sedaka, who wrote the song, and who had scored several #1 hits in his own right.