Skip to main content

It took a lot of ill-fated singles before some '50s pop stars got hits

While some lucky pop artists scored hits with their very first singles, others — including some outright legends — needed to try and try again before they finally broke through on Billboard Pop Charts. (Connie Francis famously put out 10 singles on MGM before she found success with 1958’s “Who’s Sorry Now?”) Here’s a peek at some other now-famous artists who needed at least two attempts to score chart hits back in the '50s.

By Charles Berger

While some lucky '50s pop stars hit the charts with their very first singles, others — including some outright legends — needed to try and try again before they finally broke through on Billboard Pop Charts.

Connie Francis famously put out 10 singles on MGM over the course of three years before she finally achieved chart success with 1958’s “Who’s Sorry Now?” Here’s a peek at some other now-famous artists who needed at least two attempts to score chart hits back in the 1950s.

(RELATED ARTICLE: How do Connie Francis' first 45s on MGM stack up?)

Tony Bennett

Tony Bennett photo courtesy Sony Music Archives/Don Hunstein

These days, just about everybody recognizes Tony Bennett’s name, if not his voice. But back in the 1950s, it took Bennett 11 tries to get a single on to the charts. Photo courtesy Sony Music Archives/Don Hunstein.

Born: Anthony Dominick Benedetto on Aug. 3, 1926

The crooner ties Francis for 11th time is the charm honors. Columbia released 11 singles with little success until 1951’s “Because of You,” according to the biography “All The Things You Are: The Life of Tony Bennett.” In fact, label executives told Bennett he would only get one more recording date, and he would be let go if his next record failed.

Be sure to check out Bennett’s early work on Columbia 39825, “I Wanna Be Loved” (most successfully done by The Andrews Sisters and Billy Eckstine) and “The Boulevard of Broken Dreams,” which was a hit for Jan Garber in 1934. Bennett gives his usual fine performances on both.

Pat Boone

Pat Boone photo courtesy Rhino

Before clean-cut Pat Boone turned in hit performances of songs by Little Richard, Fats Domino and The Flamingos, he recorded songs on the Republic label. Photo courtesy Rhino.

Born: Charles Eugene Boone, June 1, 1934
Pat Boone has long been vilified by critics for capitalizing on hits made by Little Richard, Fats Domino and The Flamingos. His record company (Gallatin, Tenn.-based Dot) had much to do with what Boone recorded.

And, lest you forget, the industry is meant to be a profit-making one, and if a label felt a profit could be made, why not go for it?

From 1953 to 1955 — before his tenure with Dot — Boone released four singles on the Republic label of Nashville, Tenn. His third, Republic 7084 featured the clean-cut crooner accompanied by an orchestra on the cute, uptempo “Loving You Madly” and the pleasant (if dull) flip side, “I Need Someone.”

Sammy Davis Jr.

Born: Samuel George Davis Jr., Dec. 8, 1925
Died: May 16, 1990

Sammy Davis Jr. Capitol 455364

Considered by many to be of the best all-around entertainers of all time, Davis had his first hit in 1954 with “Hey There,” which compete with Rosemary Clooney’s take and did fairly well.

But four years earlier, things weren’t quite so rosy. Davis started his recording career with several Capitol singles that went nowhere. The records are so obscure that price guides — Jerry Osbourne included — don’t even mention their existence.

When Capitol Records executive Dave Dexter heard Davis on the radio in the late 1940s, he quickly signed the performer to a contract. Davis felt the arrangements by Dave Cavanaugh didn’t suit him and he needed to demonstrate his own style.

Two of Davis’ “safe” choices are highlighted on Capitol 833: “Yours Is My Heart Alone” and “Wagon Wheels.”

Eddie Fisher

Born: Edwin Jack Fisher, Aug. 10, 1928
Died: Sept. 22, 2010
In “Been There, Done That,” Eddie (with David Fisher) relates how Eddie Cantor convinced RCA Records to extend a recording contract for its Bluebird label.

Eddie Fisher RCA 5400013

Although Bluebird folded, RCA kept Fisher on contract. His first several singles had minimum impact. In June 1950, Fisher got a break with an appearance on Milton Berle’s “Texaco Star Theater.” Later that year, he filled in for Fran Warren at Bill Miller’s Riviera in Fort Lee, N.J. Fisher did well, and his most recent record at that time, “Thinking of You,” became his first chart hit of the 1950s as a result.

But for a little blast to the past, take Fisher’s Bluebird releases “Sorry” and “Yesterday’s Roses” for a spin. These standard ballads with a chorus could have benefitted from the wonderful Hugo Winterhalter arrangements that came on Fisher’s later recordings.

Joni James MGM publicity photo with autograph

Joni James

Born: Giovanna Carmella Babbo, Sept. 22, 1930

James first recorded for Chicago’s Sharp records in 1952 with two singles: “Let there Be Love” b/w “My Baby Just Cares For Me” (Sharp 46) and “You Belong To Me” b/w “Yes, Yes, Yes” (Sharp 50).

MGM Records’ musical director Lew Douglas noticed James on a local TV program and signed her to the label, where she re-recorded “Let There Be Love.” Both Sharp singles were reissued on MGM. “Let There Be Love” features her cool pronunciation of ”chili con carne,” and “My Baby Just Cares For Me” has a nice, jazzy sound.

When it came to James’ third single, “Why Don’t You Believe Me,” there was no doubt that the fine arrangement and James’ appealing voice would make the single a smash hit, and, indeed, it was.

Johnnie Ray

Johnny Ray photo courtesy Heritage Auctions

This photo of Johnnie Ray, inscribed and signed “To Joan, My Love, Johnnie Ray” sold for $38 earlier this year via Heritage Auctions. It was part of a display that included a Clover Club flier. Photo courtesy Heritage Auctions.

Born: John Alvin Ray, Jan. 10, 1927
Died: Feb. 24, 1990
It was clear early on that Johnnie Ray caught was a one-of-a-kind performer. He was dubbed the “Nabob of Sob,” the “Prince of Wails” and “Mr. Emotion” for a good reason.
Ray was singing at a nightclub in Detroit when he impressed song plugger Bernie Lang and local deejay Robin Seymour. In turn, Seymour persuaded Danny Kessler of Okeh Records (a Columbia subsidiary that primarily was a label for R&B artists) to sign Ray. His first single, “Whiskey & Gin” b/w “Tell The Lady I Said Goodbye” does have an R&B sound.
Ray caught the public’s attention, including that of Columbia’s Mitch Miller, who had the singer record “Cry” on Okeh; the song had earlier been recorded by Ruth Casey.
Sixty-three years later, Ray’s performance of “Cry” remains impressive.
By the end of the 1950s, Ray’s single style lost its uniqueness. He became an alcoholic and died of liver failure in 1990. GM