Automotive History: The Cars of Frank Sinatra

(first posted 2/17/2012)     Aside from my well-known love of old cars, I am also a huge fan of Frank Sinatra.  From his early days as The Voice to his twilight in the 1990s, Ol’ Blue Eyes was a singular force in the world of music.  I have always been interested in the cars of all of my favorite musicians.  Unfortunately, this information is usually very hard to come by, if available at all.  Fortunately, Sinatra’s life is well enough documented that we can at least find a few of them.

Sinatra got his big break in 1939 when he signed with the Harry James big band.  His first recording with the band (All Or Nothing At All) only sold about 8,000 copies that year, but it would go on to sell millions as he became better known.  It seems that through his life, Frank Sinatra was, at least part of the time, a Chrysler guy.  Although I have not verified this recently, I recall reading in a biography that when he got married to his first wife Nancy in 1939, they went on their honeymoon in a 1939 Chrysler.

Sinatra became famous with the Tommy Dorsey Orchestra and, in 1942, began his solo career.  The Voice, as he was known then, had a string of hit records and could send most any teenage girl into a faint.  What was he driving in those years?  I have to speculate here, and if guessing, wouldn’t it have to be a Lincoln Continental?  After all, if all the other big stars like Rita Hayworth had one, surely Sinatra did as well.



Some say that the greatest single record Sinatra ever recorded was I’m A Fool To Want You.  Recorded in 1951 during a long, slow decline in his popularity and during his tumultuous relationship with Ava Gardner, Sinatra did the song in a single take.  Then, without saying a word, he strode out of the Columbia Records studio into the night.  Wouldn’t a real fan want to know what car he got into?  It bothers me that I cannot complete this mental image.  I like to think that maybe it was a new Hemi Imperial, but I am probably dreaming.

But I can move us into the high-flying 1950s when he revived his career with a fresh artistic wind.  A series of successful records backed by Nelson Riddle on the Capitol label and starring roles in a series of critically acclaimed films, he was at the top of his game.  In 1955 he recorded what is, in my opinion, one of the best up-tempo albums of his career – Songs for Swingin’ Lovers.  And that year, he did his own swingin’ in this 1955 Thunderbird.

By the next year, he was moving up.  In 1956, he co-starred with Grace Kelley and Bing Crosby in High Society, a remake of the 1940 Cary Grant-Katherine Hepburn picture The Philadelphia Story.  With the combination of Cole Porter’s songs and Sinatra’s voice and natural acting abilities, the movie was a huge hit.  Sinatra moved into automotive High Society with his next car, a Continental Mark II.  At $10,000 in 1956, this was the car that Henry Ford II used to try to put Lincoln back onto the prestige car map.   Although the Mark II failed at this mission, it was quite a car.  And Sinatra had one.

Sinatra’s dice remained hot in 1957.  His best remembered work of the year is probably his Capitol album Come Fly With Me.  I have always loved the Lockheed Constellation on the cover.  The album’s theme was a musical trip to exotic places, and then back home.  Sinatra’s Dual Ghia was sort of an exotic place all by itself.  The car is an interesting mix of Virgil Exner’s designs, Ghia’s prototypes and Chrysler drivetrains.  It is an interesting story that we do not have time for on this tour.

1958 brought the acclaimed album Only the Lonely, a classic collection of songs about heartbreak.  The 1958 Cadillac Eldorado Brougham was a kind of heartbreak for Cadillac, as the division lost a ton of money on each one of the $14,000 cars.  The Eldo Brougham was a semi-custom built four door hardtop with suicide doors and a stainless steel roof.  This is the one that graced the Sinatra garage.

By 1962, Sinatra was continuing his upward mobility.  He now owned his own record label, Reprise Records, and his albums continued to spin on turntables everywhere, at least everywhere where there were adults and martinis.  That same year, The Manchurian Candidate hit the movie screens in what became one of his most critically acclaimed movies.  Sinatra’s Chrysler thread picked up again with the 1962 Dual Ghia L6.4, the second generation of Chrysler-powered semi-customs.

Frank Sinatra turned 50 in 1965.  Everyone has a mid-life crisis, I suppose, and I guess he did too.  This customized Mustang would seem to fit the bill for a midlife crisis car.

But apparently not.  By 1969, he retired, he married a much-younger Mia Farrow (for whom he reportedly bought a 1969 Mark III) and he went way out there for his next car.  A 1969 Lamborghini Miura.

In 1980, Sinatra turned 65 and was enjoying a resurgence in his popularity and seemed to be returning to his musical and cultural roots.  He had a hit song (New York, New York).  He had a hit album (Trilogy).  And even a new movie (The First Deadly Sin).  And, of course, we know that he spent some time in his own 1981 Imperial (CC here).  Does his musical commercial count as a hit?

But what was his last car?  The answer will surprise you – it did me.  Life has a way of coming full circle, and Sinatra’s automotive history does the same.  His last car is reported to be a 1985 Chrysler LeBaron Town and Country wagon.  Even Frank Sinatra eventually put the old flash and swagger aside as he got older and could be satisfied with a very modest car.

So, as it turns out, Frank Sinatra really was a Chrysler man at heart.  Or maybe the T&C was a warranty replacement for the ’81 Imperial?