Dean Martin: Cool Then, Cool Now (2011)

Dean Martin: Cool Then, Cool Now, released in 2011.

Christmas Day 2025 will mark the 30th anniversary of Dean Martin’s passing, but the entertainer remains a suave icon of eternal coolness. Martin’s smooth singing voice, combined with his effortless charm and humor have assured him a secure spot in the pop culture pantheon. Dino has also become a Christmas staple—during the Christmas 2024 season, four of Martin’s seasonal songs charted on the Billboard “Holiday 100” chart, and his version of “Let it Snow! Let it Snow! Let it Snow!” peaked at number 8 on the Hot 100.  

The 2011 2-CD set Dean Martin: Cool Then, Cool Now, is an interesting collection. The 2 CDs are housed in a beautiful hardcover book that replicates a photo album. For Martin fans, it’s worth buying for the book alone, which reproduces many wonderful snapshots of Dean on high quality glossy paper.  

Dean Martin was many things: a comedian, a serious actor, a singer, a TV star, a nightclub entertainer, a passionate golfer, and a family man. Fittingly, the songs on the two discs are arranged thematically rather than chronologically: “The Entertainer,” “The Family Man,” “The Man-About-Town,” “The Sportsman,” and “The Movie Star.”  

My only complaint about Dean Martin: Cool Then, Cool Now is that at a mere 28 tracks spread across 2 discs, it could have been more comprehensive. Many more songs could have fit on these 2 discs. Of the 28 tracks, 7 are from Martin’s Capitol Records years (1948-1961) and 21 are from his years on the Reprise Record label (1962-1985). The booklet is sadly lacking in information about the songs—when were they recorded? What album was this song originally on? You won’t find out, unfortunately.  

Martin’s three biggest hit singles are here: “Everybody Loves Somebody,” “That’s Amore,” and “Memories Are Made of This.” But there are lots of hits that are missing: “Return to Me,” “On an Evening in Roma,” “I Will,” “Houston,” “The Door is Still Open to My Heart,” and “In the Chapel in the Moonlight” are nowhere to be found, which means that Cool Then, Cool Now doesn’t quite function as a Greatest Hits album. Maybe that’s okay, because there are so many other Dean Martin compilations. Maybe Cool Then, Cool Now is best understood as a kind of “Dean Martin 201,” a more advanced class to take after you’ve mastered the basics.  

What’s really missing from Dino’s discography is a 3 or 4 disc set that includes all of his big hit singles as well as focusing on some of his best album tracks and more overlooked songs. (I have some thoughts about what the track listing for this could look like. Give me a call, Dean Martin Family Trust!)  

Similar to the 2012 Collected Cool set, Cool Then, Cool Now unfortunately overlooks Dino’s later career, as it features only one song from Martin’s 6 albums from the 1970’s, and nothing from his final 1983 album The Nashville Sessions. But both collections get points for including Dean’s final recording, the 1985 single “L.A. Is My Home,” a fun song that finds Dino still in great voice.  

Okay, I’ve complained enough about what songs aren’t included, so I should probably tell you more about what songs are included on these two discs. There are two overdubbed “duets” on Cool Then, Cool Now. The less said about “Ain’t That a Kick in the Head” with Kevin Spacey, the better. But the other duet is a delight, “Please Don’t Talk About Me When I’m Gone,” with the British singer Robbie Williams. Williams, who has curiously never had much chart success in the US, is a big fan of Dean Martin, and his voice mixes well with Dean’s.  

One song that was a prescient pick was “Mambo Italiano,” a hit for Rosemary Clooney that is now one of Dean’s most popular songs on Spotify, with 71 million streams. “Snap Your Fingers,” from Martin’s 1965 album Houston, is an excellent song that deserves the prominent placement it receives here. Dean’s 1966 version of “I’ve Grown Accustomed to Her Face,” from The Dean Martin TV Show album, is a treat. Beginning with just Dean’s voice and Ken Lane’s piano, you can really appreciate the beauty of Dean’s singing. The same goes for “Gimme a Little Kiss, Will Ya Huh” from the wonderful Dream with Dean LP.  

Disc 2 features 4 terrific country songs that were recorded for Dean’s 1965 LP (Remember Me) I’m the One Who Loves You: “Welcome to My World,” “Born to Lose,” “Bumming Around,” and “King of the Road.” Given that Dino was almost always attired in a tuxedo on his TV show, he might have seemed an unlikely candidate to sing “Bumming Around” and “King of the Road,” both songs about riding the rails, but his versions of these songs are superb. They are a testament to Martin’s interpretive abilities.  

Several songs on Disc 2 are from Martin’s movies. They have rarely been included in collections, so they’re a treat to have. They include “Five Card Stud,” from the Western of the same name, starring Martin and another figure of mid-century cool, Robert Mitchum. Coincidentally, Mitchum and Martin both had hits with the song “Little Old Wine Drinker, Me.” Mitchum had a hit with the song on the Country charts, and Dino’s version was a hit on the Pop charts. “Any Man Who Loves His Mother” is from the Rat Pack movie Robin and the Seven Hoods, and “Side by Side,” “The Glory of Love,” and “Red Sails in the Sunset” are all from the first Matt Helm movie The Silencers.  

Dean Martin: Cool Then, Cool Now, offers ample evidence of Dean Martin’s charm, charisma, and winning way with a song.