What pre Rock and Roll performer has had most recent hit?

[DChord568]

@Ellis_Aponte_Jr

You need to have a #1 hit before July 9, 1955 to qualify, which Johnny Mathis and Henry Mancini never had. Mancini charted no singles before 1960, although his Peter Gunn album was a #1 in 1959.

Sammy Davis Jr. is almost a winner, though. His recording of “Hey There” was a #1 on the Cashbox chart in 1954, but not in Billboard. This is sort of a technicality, however, since these were the days when different artists would release their version of a song simultaneously, causing ambiguity, and Billboard happened to credit Rosemary Clooney with a #1 for her contemporaneous version of the same song.

Interesting anomaly, but Davis’s version of “Hey There” did get an official chart position on Billboard (#16). So he can’t really work. “Candy Man” was in fact his first #1.

[DChord568]

@MentalGuy

A month or so ago, we were taking a trip and I was listening to the “70’s on 7” channel on satellite radio. They were playing an episode of American Top 40 from 1973. I was a little surprised when I heard Perry Como on the charts in that year. He was singing Don McLean’s “And I Love You So.”

This got me to wondering, what is the most recent hit by a performer who had a number one hit before the rock and roll era?

Actually, let’s make this a bit more specific. What performer that had a number one hit on the Billboard pop chart before July 9, 1955 has had the most recent:

A) top 40 hit?
B) top 10 hit?

For B, you almost answered your own question!

Perry Como, who had quite a few pre-1955 #1 hits, made it to #10 with “It’s Impossible” in 1971.

[DChord568]

@MentalGuy

Actually, let’s make this a bit more specific. What performer that had a number one hit on the Billboard pop chart before July 9, 1955 has had the most recent:

A) top 40 hit?
B) top 10 hit?
C) number 1 hit?

And for C, I believe it’s the aforementioned Frank Sinatra, for “Somethin’ Stupid” with Nancy in 1967.
So, in summary:

A) Nat ‘King’ Cole, “Unforgettable” (#14, 1991)

B) Perry Como, “It’s Impossible” (#10, 1971)

C) Frank Sinatra, “Somethin’ Stupid” (#1, 1967)
In the case of A and C, IMHO the presence of the artist’s name on the record label is enough for me, regardless of any accompanying “and”'s or “with”'s.