Automotive History: The Cars of Frank Sinatra

Frank Sinatra Owned this LA House with a 20 Car Parking

House has a 4 car garage and according to the listing agent it has total parking for 20 cars. It also has a large motor court which is highly sought after in Los Angeles real estate.

This is a premier property in a perfect Holmby Hills location. On over 2 park-like acres of rolling private grounds. Older hacienda could be remodeled/restored or build an amazing estate in a neighborhood of incomparable homes.

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.

1942 Chrysler Convertible

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.

This is the 1957 Dual Ghia convertible

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.

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.

1958 Cadillac Eldorado Brougham - $122,500

In August 2009, a 1958 Cadillac Eldorado Brougham which was owned by Sinatra was sold at a Bonhams auction in California. It sold for $122,500. Only 504 examples of this car were built between 1957 and 1958.

One previous owner of the car, a former California Highway Patrol officer, has spoken of how he stopped Sinatra in the vehicle back in 1958 for speeding. Years after this incident, the officer’s half brother bought the car at auction and gave it to the officer as a gift on the condition that he drive and enjoy it.

This is the 1961 Dual Ghia Coupe

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.

1961 Rolls Royce Silver Cloud II - This car has a distinctive gold plated "Flying lady" mounted on the front grill. It has turn signals mounted between the doors. Rolls Royce didn't offer many options back then but Frank Sinatra requested to have the ornament gold plated.

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 Lincoln Mark III and he went way out there for his next car.

A 1969 Lamborghini Muira

1976 Rolls-Royce Silver Shadow Chassis No. SRE 24513

A peacock blue 1976 Rolls-Royce Silver Shadow once owned by Frank and Barbara Sinatra was sold at a Christie’s auction in New York in 1997 for $56,350. The sedan was a wedding present from Frank to Barbara.

At the time of the auction, the car still retained a windshield sticker for use at the Palm Springs municipal airport due to Frank and Barbara’s frequent traveling

1965 Rolls Royce Silver Cloud III

1981 Chrysler Imperial with Frank Sinatra driving

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?

1985 Chrysler LeBaron Town and Country wagon.