Its first release on record was on January 4, 1957 on a single with "Too Much" on the other side. "Playing for Keeps" reached number 34 in the United States, while "Too Much" spent 3 weeks at number 1.

In 1959 the song was included on Elvis' album For LP Fans Only (an unusual album for Presley cause all the songs on it had been already released one to almost five years prior).

The song was written by Sun Studio house band steel guitar and bass player Stan Kesler (words and lyrics), who wrote or co-wrote five songs in total for Elvis Presley during Elvis' early career: "I'm Left, You're Right, She's Gone". "I Forgot to Remember to Forget", "Thrill of Your Life", "Playing for Keeps", "I'm a Fool (For Loving You)".

Elvis recorded it on September 1, 1956 at the Radio Recorders Studio in Hollywood, California (at the studio sessions for RCA Victor that were held at Radio Recorders on September 1-3). The master recording of "Playing for Keeps" is a splice of two takes: take 7 with the ending from take 18.

Preorders for the single "Too Much" / "Playing For Keeps" reached almost 500,000 copies.

Billboard picked the single "Two Much"/"Playing for Keep" for its "Spotlight" section and then (in its January 19, 1957 issue) as one of "This Week's Best Buys":

Advance orders put this disk in the best seller class even before it was generally available. [...] It doesn't take genius to see that this will be a chart record shortly. At this early stage, it is hard to determine which side rates top listing. The Presley fans are giving both tunes quite a whirl; both are propeling it forward. A previous Billboard "Spotlight" pick.

Mike Eder states his opinion of the side "Playing for Keeps" in his book Elvis Music FAQ: All That's Left to Know About the King's Recorded Works:

"Playing for Keeps" is one of the few early single sides that wasn't worthy of the spotlight it was given. He tries too hard at putting feeling into the track, pushing his voice intoan awkward whine. Elvis didn't yet possess the kind of big voice he wanted for ballads like this, but you can't blamehim for trying to go beyond his comfort zone. The song was written by Stan Kesler, who had been a friend of Elvis' when they both worked for Sun Records. Kesler had co-composed early single sides “I'm Left, You're Right, She's Gone,” and“I Forgot to Remember toForget,” and Elvis may have recorded this somewhat dreary ballad partially as a favor to him.

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Wikipedia