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

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?
C) number 1 hit?

Tony Bennett reached #1 on the Billboard Hot 100 in 1951 with Because of You, and #22 on the Billboard Adult Contemporary charts in 2006 with Just in Time (a duet with Michael Bouble).

Johnny Cash, who just barely qualifies as “pre-Rock,” charted in 2006 in the UK with “God’s Gonna Cut You Down” and “Love’s Been Good to Me.” His last US hit, “Hurt,” was in 2003.

Nat “King” Cole had some posthumous hits with his daughter as recently as 1992, but I don’t think they’re in contention.

I believe he charted with his Duets album a few years ago as well.
ETA, it looks like the album debuted at #1 but no specific song hit #1.

There will doubtless be better contenders, but Benny Bell hit #30 with the novelty hit “Shaving Cream” in 1975. He is not only a pre-rock ‘n’ roll artist, the recording itself was made in 1946. I suspect this represents the biggest gap between a song being recorded and becoming a Top 40 hit.

ETA: Not germane to the main topic, but to the last sentence above: The Elvis Presley song “A Little Less Conversation,” first recorded in 1968, became a worldwide hit in 2002 (34 years later) in a remixed version with JXL. However, this song only made it to #50 on the U.S. Billboard charts.

If we’re talking strictly the pop Top 40 and not the Adult Contemporary chart or any other, I think Frank Sinatra may own A, B, and C.

He had #1s going back to the 1940s with such songs as “All Or Nothing at All” (a 1939 recording which became a hit in 1943). His latest #1 was “Somethin’ Stupid,” his duet with daughter Nancy, in 1967. (He’d gone to #1 in 1966 also, with “Strangers in the Night”). “Somethin’ Stupid” then may be the answer to your B and C questions.

Years later, in 1980, Sinatra broke the top 40 with “Theme from New York, New York,” which peaked at #23, so I think that’s the answer to A.

(Btw, I never knew that “Shaving Cream” was a 1940s recording - that’s amazing!)

Louis Armstrong’s recording of “What a Wonderful World” was not a huge hit in the USA when first released, but reached #32 on the Billboard charts in 1988 (more than a decade after Armstrong’s death) after being featured in the Robin Williams movie Good Morning, Vietnam.

Frank Sinatra’s last top 40 hit in the United States was “New York, New York,” which reached #32 in 1980. But in England, he reached #4 when he recorded “I’ve Got You Under My Skin” with Bono.

“Lord’s Prayer” written by Jesus, charts some 1,943 years later in 1974.

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However, although it was written by Bell and he produced the single, he did not sing it. It was sung by Phil Winston, under the pseudonym Paul Wynn. Since Bell also used the name Paul Wynn, he was mistakenly given credit for the vocal. After some controversy the single was reissued giving Paul Wynn the vocal credit.

I remember Jackie Wilson’s “Reet Petite” being a big hit (No 1 in the UK at least) in the 80’s some 30 years after it was first released.

Not a performer credit, though. The author of Ecclesiastes who wrote what became the lyrics of “Turn! Turn! Turn!” long pre-dates Jesus, for that matter, but s/he didn’t perform any of the versions that hit the charts in the last few decades.

Similarly, I’m thinking there’s got to be some classical composer whose work charted in a novelty version in recent decades, but they wouldn’t get performer credit either.

Well, by THAT standard, Beethoven had a #1 hit on the US Billboard charts in 1975! Remember Walter Murphy’s disco hit “A Fifth of Beethoven”?

Since it’s been asked "WHich pre-rock and roll artist recorded a #1 single most recently…
Does Johnny Mathis count as “pre” rock and roll? He came on the scene around the same time as Elvis, but his style wasa certainly pre-rock.

IF he counts, he reached #1 in 1978 with “Too Much, Too Little, Too Late,” a duet with Deniece Williams.

If he DOESN’T count, I’ll have to do more research.

If Johnny Mathis doesn’t count, Henry Mancini almost certainly does.

He had a #1 single in 1969 with Love Theme to Romeo and Juliet (A Time For Us)

Other “recent” #1 hits by artists from before the rock era:

1968: “Love Is Blue” by Paul Mauriat, and “This Guy’s In Love With You” by Herb Alpert
1967: “Something Stupid” by Frank and Nancy Sinatra
1966: “Strangers in the Night” by Frank Sinatra

How’d I forget- Sammy Davis Jr. reached #1 in 1972 witrh “The Candy Man” from the movie WIllie Wonka and the Chocolate Factory.

And Nelson Riddle counts even more. His trio of mid-1980s albums with Linda Rondstadt all charted on the main (not just the Jazz category) Billboard album charts, with What’s New staying there for 81 weeks and hitting #3 for five straight weeks.

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.

You’re mistakenly equating “non-rock ‘n’ roll performer” with “pre-rock ‘n’ roll performer” here.

Paul Mauriat didn’t release any recordings under his own name until 1957.

Herb Alpert began his professional career in music that same year, and in fact his first involvement was as a songwriter — of rock ‘n roll/R&B songs such as Jan and Dean’s “Baby Talk,” Sam Cooke’s “Wonderful World” and The Hollywood Argyles’ “Alley Oop.”

He made his first recording as a solo artist in 1960.

I think Nat “King” Cole wins this one if you don’t mind stretching things just a little.

The version of “Unforgettable” released in 1991 that featured his daughter Natalie on added vocals was the same instrumental and vocal track originally recorded by Nat “King” Cole in 1961 (itself a remake of his original 1951 recording). It was simply remixed to add Natalie’s vocal.

The artist credit on the record was “Natalie Cole with Nat ‘King’ Cole.” As Nat had many pre-1955 hits, including several #1’s, he qualifies under the OP’s criteria.