FAVORITE DEAN MARTIN SONGS!

A few folks in and around the entertainment industry share their favorite Dino songs!
Written By Karen Morris for The Dean Martin Association for their exclusive magazine (2024 published)
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As a long-time fan of Dean Martin, I continue to enjoy many of his endearing recordings. His smooth style, debonair demeanor, and easy-going, suave vocal artistry all point to why he is aptly known as the "King of Cool".
Considering his vast repertoire, I must admit that one song always comes to my mind when I think of Dean. The song: "Ain't That a Kick in the Head." After watching Dean perform "Ain't That a Kick in the Head" in the popular 1960 Rat Pack heist film Ocean's 11, I immediately became a fan of his, the movie, and the tune.
An alternate arrangement of that song, featuring Dean with vibraphonist Red Norvo and his quartet, is spotlighted in the film. Although another version of "Ain't That a Kick in the Head" was released as a single the month before the film premiered.
The swingin' single blends the lyrics by Sammy Cahn and music by Jimmy Van Heusen with a marvelous arrangement by conductor Nelson Riddle. Along with Dean's carefree delivery, it's a winning combination and remains my favorite song sung by Dean.
Over the years I've met fans of Dean who suggested other melodies that reminded them of him, or one they especially favored.
To further explore this, I reached out to a few folks in and around the entertainment industry and asked their opinion. (A shout-out of thanks to those who were kind to respond!!)
Below are their song-pick responses and a few shared anecdotes about Dean:
Tom Dreesen
Comedian who toured with Frank Sinatra for 13 years as Sinatra's opening act, has over 500 appearances on national TV and over 60 appearances on The Tonight Show.
Song Pick: "Ain't That a Kick in the Head"

Karen, As you know I knew Dean and performed with him on a couple of private events as well as doing a couple of the Dean Martin Roasts. On a personal note he gave me some advice while we were on a gig in Sacramento, Ca. I was in his dressing room before the show and the subject came up about "Mob Guys" who owned clubs or were connected to charities and would ask you to come and perform for them. Dean said "Tommy don't let them do a favor of any kind for you. It's okay to do a show and get paid for your performance but nothing outside of that. Bottom line is don't ever get indebted to them even in a small way" I followed his advice throughout my career.
2nd story from Tom:
Sammy Davis Jr. sometimes used a teleprompter whenever he was singing new material—maybe a cover of a song by another artist or an obscure Broadway show tune. As someone who had seen Frank at the top of his game for so long, it occurred to me that maybe Frank should employ a teleprompter like his buddy Sammy, just in case. I didn't want to be the one to suggest this, so I gently floated the idea with Hank Cattaneo, who agreed and finally persuaded Frank to give it a try.
Teleprompters, when positioned strategically on the stage, look like feedback monitors to the audience. Frank could glance down casually at a teleprompter and see the next lyric, and it would seem like he was just looking at the audience. He was very good at the technique, and there were times when he didn't even look at the teleprompters, but they served a purpose as a security blanket. He was more comfortable knowing the words were there. He was like a new man onstage and more confident—to the point that he brought back songs to his live shows that he hadn't done in years. Encouraged by what the teleprompters had done for his shows, Frank started encouraging other showbiz pals to try them out, beginning with Dean Martin, who was reportedly having trouble himself in Las Vegas, forgetting lyrics and quitting halfway through some songs.
Frank said, "Look, you know we're getting older, and you should use those teleprompters." But Dean just dismissed him. Dean was a tough sell, and he humorously feigned indignation that Frank had even suggested that he needed assistance onstage, but Frank persisted.
One day, we were appearing at the Fox Theatre in Detroit. We had done a matinee, and we had an evening show to do. We were sitting around Frank's suite watching football when Frank got a call from Mort Viner, Dean's manager, who said that Dean had used a teleprompter the night before in Las Vegas and loved it. According to Viner, as Dean came offstage that night, he said, "Book me on a world tour!" Frank smiled and said, "Damn it, he's finally listening to me! Get Dean on the phone." Viner got Dean on the phone, and Frank started chewing him out. He said, "Goddammit, Dag..." (He always called Dean "Dag," an affectionate term among the two of them.) "I've been telling you for years, we're not getting any younger. So, what if you've gotta use those teleprompters? For Chrissake, we're not kids anymore...." Dean wasn't about to admit that Frank was right. He didn't want to hear the gloating. Dean said, "Yeah, yeah, yeah.... Hey, where are you guys tonight?" And Frank said, "Hold on one second. Hey, Tommy, where're we at?" I reminded him we were in Detroit. Frank said, "Detroit." And Dean said, "Well, did you have to look in the fucking teleprompter to see what city you're in?"Frank dropped the phone and with a huge laugh he roared, "Dean did it again! The bastard got me again!"
As for my favorite Dean Martin song I find myself singing "Ain't That A Kick In The Head"

Brook Babcock
President of The Jimmy Van Heusen Music Corporation, Grand-nephew of Jimmy Van Heusen
Songs: "Ain't That a Kick in the Head" and "Heaven Can Wait"

Hi Karen
My first favorite Dean Martin song is no surprise!
"Ain't That A Kick In The Head"
Music by Jimmy Van Heusen and Lyrics by Sammy Cahn, from the movie Ocean's Eleven starring Frank Sinatra, Dean Martin, Sammy Davis, Jr, Peter Lawford and Angie Dickinson originally airing in 1960. This song is still as relevant as it wasback then. In the last several years it has played in
commercials in the Super Bowl, along with many other movies and TV shows.

My second favorite Dean Martin song is lesser known today: "Heaven Can Wait"
Music by Jimmy Van Heusen,Lyrics by Eddie DeLange.This was the first song that Jimmy Van Heusen
co-wrote that made it to number one on the Hit Parade. Originally written in 1939 for a Broadway show that did not happen. Dean Martin featured his version in 1960 with This Time I'm Swingin' album release.
Charles L. "Chuck" Granata
Author, Music Historian and Archivist, Record and Radio Producer, Host of Sinatra Standard Time Song: "Hit the Road to Dreamland"

There are so many wonderful songs that Dean made his own - and he could sing practically anything and impart something nuanced and unusual. One of my very favorites is "Hit the Road to Dreamland" from his Capitol album 'Sleep Warm,' on which the orchestra was conducted by...Frank Sinatra! I love the song (which Sinatra never sang), and the pictures of them working together in the studio are pretty cool, too.
Jay Kogen
Emmy Award-winning comedy writer, producer, actor and director. (Writer for Frasier, Malcolm In The Middle, Everybody Loves Raymond; Original Writer and Co- Executive Producer of The Simpsons)
Song: "Ain't That a Kick in the Head"

"Ain't that A Kick In The Head" is one of the best big band arrangements Dean ever sang. It's very ratpack. Upbeat and fun. Like Dean. When I was 5 I met Dean Martin. Well, I was near Dean Martin. I was an extra on a Christmas special. My father was a writer on the show and they needed kids for a big song. All the children of the people who worked on the show were there for two days. Dennis Weaver was doing a number with Dean. But we never saw Dean Martin. It was just Dennis and Dean's stand-in until the night we shot. Then Dean shows up. He sings. They sing. He senses where to go. He knows the song. He sounds great. He's got the delightful charm that you see on TV. All charm and fun. At one point Dean picks up my sister and sings to her. My sister is unimpressed which makes Dean all the more happy. She's real and he seems to prefer that to someone who's a crazed fan. It was my first taste of show business and it was when I decided I wanted that fun carefree creative experience and I've been chasing it ever since.
Mary Caldwell
Wife of popular singer, songwriter and musician, the late Bobby Caldwell. Known for his hit single, "What You Won't Do For Love", and Vice President of Bobby Caldwell Entertainment LTD.
Song: "Embraceable You"

Thanks so much for remembering Bobby. His favorite Dino song was, "Embraceable You." That is my favorite too!!
Sal Scognamillo
Executive Chef/Co-owner of Patsy's Italian Restaurant NYC, Frank Sinatra's favorite restaurant
Song: "Everbody Loves Somebody"

I would say "Everybody Loves Somebody"
Bill Boggs
Emmy Award-winning TV talk show Host, Producer and Author Song: "La Vie en Rose"

"La Vie en Rose ". From the Dean LP " Dean Martin French Style" is my longtime favorite.
Erik Tarloff
Award-winning screenwriter, playwright and novelist Song: "Two Sleepy People"

I've always liked the duet with Line Renaud of Hoagy Carmichael's "Two Sleepy People."
Darren Grubb
Strategic Communicator, Media Relations professional, Co-Author of legendary comedian Tom Dreesen's celebrity memoir. Song: "I Will"

First some DG trivia: I'm named after Bobby Darin...and Dean Martin (Dean is my middle name). Always proud to make that connection when I have the chance.
My favorite Dean vocal recording is "I Will," written by Dick Glasser and first performed by Vic Dana in 1962. Dean recorded it in 1965 and it reached #10 on Billboard's Hot 100. Just a great song that, like so many of his recordings, showcases Dean's confidence and skill as a singer. You can almost hear him smile on the track. The orchestration was top-notch, too.
Brian Mark
Executive Producer of The Sounds Of Sinatra Radio Program and son of legendary broadcaster Sid Mark
Song: "On An Evening in Roma"

Hearing Dean sing in Italian (and combined with English on this track) adds an incredible dose of authenticity. Every time I hear it, I feel like I can see what he is singing about. It's timeless, traditional and .... it's Dean.
I can't think of a particular Dean track that Sid Mark loved, but I do know he loved it when Dean and Frank sang together.
Dana Polan
Martin Scorsese Professor of Cinema Studies, Tisch School of the Arts, New York University
Song: "My Rifle, My Pony and Me"

My favorite is a duet, "My rifle, my pony, and me" which DM sings with Ricky Nelson in Rio Bravo. DM actually is fabulous in the film as an actor and the song helps show how the good guys bond at a crucial moment in the film.
Mark Sudock
Host & Producer, THE SINATRA SONGBOOK, Metromedia Radio
Song: "Dream with Dean" album; "The Things We Did Last Summer"

For my money, Dean's at his very best when he sings softly and intimately. His 1964 Reprise album, "Dream with Dean" is filled with such moments. Ken Lane (piano), Barney Kessel (guitar), Red Mitchell (bass) and Irv Cottler (drums) provide the gentle accompaniment. "I'm Confessin' That I Love You", "I'll Buy that Dream", "I Don't Why (But I Do)", "My Melancholy Baby" and "Smile" illustrate this side of Dino exquisitely. And from Dean's 1966 reprise release. "The Dean Martin Television Show", consider "The Things We Did Last Summer". These examples offer a distinctive side of this great entertainer. Wonderful stuff.
Howard Murray
Television Director whose credits include The King of Queens, The Big Bang Theory Two and a Half Men among others. Son of famed comedian Jan Murray who performed with Frank Sinatra, Dean Martin Sammy Davis Jr. at Carnegie Hall in 1961 "(Tribute to Martin Luther King Jr.)
Song: "Everybody Loves Somebody


My favorite would have to be 'Everybody Loves Somebody Sometime'. It reminds me of our family vacation to Las Vegas when Dad (Jan Murray) was appearing there. Sitting by the pool every day, I'd hear that song. Still makes me smile.
Christopher Riddle
Conductor/Music Director of The Nelson Riddle Orchestra for the past 39 years, since his father's passing in 1985.
Song: "Ain't That a Kick in the Head"
My favorite is Ain't That a Kick in the Head. (Christopher's dad, Nelson Riddle, arranged that song for the film Ocean's 11, as well as the entire film score.)

Special Mention Song: Don't Be a Do-Badder - From Robin and the 7 Hoods. Bing Crosby sings the song in one scene; the song is performed in the finale, by Frank Sinatra, Dean Martin and Sammy Davis Jr.) (Nelson Riddle arranged/ conducted)

Christopher Riddle had mentioned the song to me, as well as to Geoffrey Littlefield in the book "Nelson Riddle - Music With a Heartbeat"
"Skip, Rosemary and I went along with our father (Nelson Riddle) to one of the recording sessions where Bing and Dean were performing (Don't Be a Do-Badder). We were out there at Warner's for the recording of the music for Robin and the 7 Hoods. I went a number of times to observe the underscoring and used to hang out in the green room and go to lunch with them, and also helped out in Frank's office (he had an office at Warner Bros.). His production company at the time was Seven Arts. I was 13 years old." (*Adding Chris also told me their sister Bettina was at the recording session as well.*)