What Rat Pack Songs Will They Sing on Tonight’s ‘The Masked Singer’?
Not every member of the Rat Pack — a group of swingin’ ’50s and ’60s stars who worked and played together, like Frank Sinatra, Dean Martin, Sammy Davis Jr., Joey Bishop and Peter Lawford — sang. But singers Sinatra, Martin and Davis were each responsible for some of the 20th century’s most beloved and enduring songs — which is why they’re being honored on tonight’s “Rat Pack Tribute Night” episode of The Masked Singer, airing at 8pm EST on February 26, 2025.
We don’t know exactly which songs will be performed yet (though a clip of Ant singing Peggy Lee‘s “Fever” was included in the episode teaser). But you can read on for a primer on the Rat Pack’s greatest songs — you’re guaranteed to hear at least a few of these tonight.
Frank Sinatra
“Strangers in the Night”
Considering that Sinatra is one of the most famous singers of all time, you might be surprised to learn that he only had two number one songs in his lifetime! His first was 1966’s “Strangers in the Night,” which also won him Grammys for Best Male Pop Vocal Performance and Record of the Year (his second was a year later — “Somethin’ Stupid,” his duet with daughter Nancy Sinatra).
The song originated as a wordless orchestral piece created for the soundtrack of the 1966 James Garner/ Sandra Dee movie A Man Could Get Killed; one of Sinatra’s producers heard it and thought it could be turned into a great track for Old Blue Eyes. The lyrics took inspiration from the film, which began with James Garner exchanging glances with his female co-star, who became his girlfriend by the end of the film.
“My Way”
Possibly Sinatra’s most famous tune, this song has a surprising back story — it’s an English-language translation of a French song called “Comme d’habitude,” and the English lyrics were written by none other than Paul Anka! Sinatra famously recorded his 1968 version in a single take.
The song peaked at 27 on the Billboard charts, but became Sinatra’s most memorable hit for many — a situation that Sinatra himself was supposedly not happy about. According to his daughter Tina, “He always thought that song was self-serving and self-indulgent.”
“New York, New York”
This classic, which Sinatra typically sang to close out his concerts, sounds like it should be from his classic ’50s and ’60s era. But this tune is actually from 1980! It originated in 1977, as the theme of Martin Scorsese‘s unsuccessful musical, New York, New York — Liza Minnelli sings the song in the film. Minelli’s version peaked at #104 on the Billboard charts; a friend of Sinatra’s passed the music on to him, and he recorded it in 1980, picking up a Grammy nomination for Best Pop Vocal Performance, Male.
Dean Martin
“That’s Amore”
Martin’s first signature hit first appeared in the 1953 film The Caddy, where Martin starred alongside longtime comedy partner Jerry Lewis. In the film, it is sung primarily by Martin, with Lewis eventually joining in. It was nominated for an Oscar that year for Best Original Song. The song never charted in the US, but has gone platinum.
“Everybody Loves Somebody”
Martin’s 1964 hit had already been recorded by a number of other artists — including Frank Sinatra! — when he released it as single. Though Martin had not had a major hit for close to a decade at that point, “Everybody Loves Somebody” was so popular, it knocked the Beatles’ “Hard Days Night” out of the Billboard number one slot. The song became Martin’s signature, which he sang regularly on his TV show; its lyrics are even inscribed on his gravestone.
Sammy Davis Jr.
“The Candy Man”
Davis was decades into his career, and nearly 50 years old, when he recorded his signature hit, which was released in 1972, and hit number one two weeks in a row — his only top 10 hit. Though Davis himself was supposedly not a fan of the song — after recording only two takes of the song, he reportedly said, “This record is going straight into the toilet … and it may just pull my whole career down with it.”
And no, your ears are not deceiving you — it’s the same song sung in 1971’s Willy Wonka and the Chocolate Factory. The song was written specifically for the film, and recorded originally by Aubrey Woods, who plays Bill the candy store owner in the film.
Peggy Lee
“Fever”
Peggy Lee was not technically a member of the Rat Pack. But she was a contemporary and sometimes collaborator of the group, who performed and dueted with Sinatra and Martin. In the “Rat Pack Tribute” episode trailer, Ant is shown singing Lee’s signature hit “Fever” — a song that Lee didn’t originate, but did make her own.
“Fever” was originally released by R&B singer Little Willie John in 1956, in a fairly different style; Lee changed some lyrics and created her own arrangement for her sultry, torchy version. Though the song peaked at number 8 on the Billboard charts when it was released, it has become Lee’s legacy, and remains one of the most popular pop songs from the mid-20th century.
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1950s Musicals
November 2020
Bright and brassy, toe-tapping musicals from the 1950s
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