17 Iconic Cars from Frank Sinatra’s Collection That Showcase His Impeccable Taste

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Few artists have left as great an impression on 20th-century popular music as Frank Sinatra. From his humble beginnings in Hoboken, New Jersey, to the bright lights of Manhattan and the Las Vegas Strip, Sinatra became a dominant musical force thanks to his distinctive voice and big band-style jazz-inflected songs that could be loosely categorized as swing.

1. **Chrysler Convertible**: Sinatra was among the many “boy singers” in the New York area seeking the “favorable moment.” He got his first break with the group The 4 Flashes in the mid-‘30s, according to James Kaplan’s memoir The Voice, not due to his musical talent but because he had a car—the green Chrysler convertible. With Sinatra and his charming Chrysler on board, the ensemble had an easier time booking performances. Sinatra was already on the fast track to stardom.

2. **1942 Chrysler Convertible**: Sinatra remained a Chrysler man even after achieving fame. Rich with nostalgia, he drove off to his honeymoon in a brand-new 1939 convertible when he married his first wife, Nancy Barbato. Sinatra is shown triumphantly behind the wheel of a 1942 convertible, one of only 36,586 cars Chrysler managed to produce before manufacturing was paused due to World War II. These vehicles are now highly collectible, even without Sinatra’s connection, selling for significant amounts at auctions.

3. **1955 Ford Thunderbird**: Sinatra’s career was on an upswing in the early 1950s, and by the mid-decade, he had won numerous accolades and amassed considerable wealth, fueling his passion for cars. He was pictured often in a black first-generation Thunderbird, which he bought from Capitol Records. Rumor has it he also gifted T-Birds to his close friends and favorite girlfriends, showcasing his generous spirit.

4. **1956 Continental Mark II**: The Continental Mark II is recognized as one of the most beautiful luxury cars of its time. Priced at $10,000, it was twice as expensive as a Cadillac and more than the Rolls-Royce Silver Cloud, yet Ford lost money on each one sold. Sinatra was a natural fit for the Continental II, complementing his lifestyle of exclusivity and elegance, often spotted driving it in Las Vegas and Palm Springs.

5. **1958 Cadillac Eldorado Brougham**: Cadillac responded to the reintroduction of the Continental by launching the Eldorado Brougham, which became a symbol of luxury and sophistication. With advanced features like self-leveling air suspension and dual-level climate control, it was the car to have in the late 1950s. Sinatra loved the Brougham so much that he owned several, one of which even appeared alongside him in “Ocean’s Eleven.”

6. **1962 Dual Ghia L6.4**: By the early 1960s, Sinatra had cemented his status as a Las Vegas legend, and his vehicle choices reflected that. The $13,500 Dual Ghia L6.4 was one of the rarest cars with only 26 produced, most of which went to celebrities. Its unique design combined Chrysler components with handcrafted Italian artistry. Sinatra’s car was distinctive with custom features added by famed customizer George Barris.

7. **1969 Lamborghini Miura**: On his 54th birthday, Sinatra treated himself to a Lamborghini Miura, often regarded as the world’s first supercar. He ordered it in his favorite color, arancio metallico, and even enjoyed a luxurious interior. Sinatra’s love for the Miura was profound, famously stating that you buy a Ferrari to be someone, but a Lamborghini when you already are someone. However, he later gave it to a girlfriend who traded it in for a newer model.

8. **1976 Jaguar XJS V-12**: After marrying Barbara Marx, Sinatra received a British racing green XJS as part of their wedding gifts. This grand tourer replaced the aging E-Type and became a reliable vehicle during its long production run. Sinatra liked it so much that he added a second similar model to his collection a few years later, showcasing his fondness for the luxurious ride.

9. **1981 Chrysler Imperial ‘FS Version’**: Sinatra’s connections within the automotive industry led to the creation of the Imperial “FS Edition,” which featured bespoke paint and interior colors that matched his eyes. Despite high expectations, the model flopped in the market, selling only 12,385 units. Nevertheless, it remains a treasured piece of automotive history, symbolizing Sinatra’s enduring legacy in the automotive world.

10. **1985 Chrysler Town & Country**: Sinatra’s last car was a 1985 Chrysler Town & Country station wagon. While it lacked the glitz of his earlier rides, he seemed to enjoy its practicality in Los Angeles, and it was reported to be the final vehicle he ever drove before his passing in 1998. This modest choice highlights the full circle of Sinatra’s automotive journey, from luxurious cars to a more humble end.

11. **Chrysler LeBaron**: As Frank Sinatra’s final foray into the world of automobiles, the 1985 Chrysler LeBaron Town & Country station wagon serves as a poignant reminder of his incredible journey. While this car may not have the same flair as some of his previous rides, it resonated with Sinatra’s practical side. He reportedly enjoyed the spacious and functional design, reflecting a shift from his earlier luxurious choices to something more family-friendly. This vehicle, with its classic wood paneling, was a fitting end to Sinatra’s motoring saga, providing the comfort he needed in his later years.

12. **1954 Cadillac Eldorado**: Before the iconic 1958 version, Sinatra had a taste for luxury in the form of the 1954 Cadillac Eldorado. This car was one of the first to feature the prestigious Eldorado nameplate and boasted a striking design that screamed elegance. With its long hood and sleek lines, the 1954 Eldorado represented the height of post-war American automotive design. Sinatra, known for his flair, would have resonated with this vehicle’s captivating presence on the road, reinforcing his status as a cultural icon.

13. **1961 Mercedes-Benz 300SL**: Known as the ‘Gullwing,’ the 1961 Mercedes-Benz 300SL was a masterpiece of engineering and aesthetics, making it an obvious choice for someone of Sinatra’s stature. Its unique doors and impressive performance set it apart, capturing the hearts of car enthusiasts worldwide. Sinatra, with a penchant for the extraordinary, would have reveled in the power and prestige that came with owning such a legendary automobile, embodying the glamorous lifestyle he was synonymous with during his peak years.

14. **1970 Chevrolet Corvette**: In the 1970s, Sinatra embraced a more youthful spirit with the purchase of a Chevrolet Corvette, a symbol of American muscle and freedom. This car was more than just a mode of transportation; it represented style and daring. Sinatra’s decision to drive this sports car speaks to his desire to maintain a youthful image while navigating the complexities of fame, showcasing his ability to adapt and redefine his persona throughout his life.

15. **1987 Cadillac Allante**: Sinatra’s later years also saw him behind the wheel of a 1987 Cadillac Allante, a luxurious convertible that was praised for its Italian design influence. This car, known for its elegance and performance, was a testament to Sinatra’s enduring love for luxury vehicles, even as trends shifted. The Allante’s sleek lines and opulent interior would have appealed to Sinatra’s sophisticated taste, allowing him to enjoy the finer things in life until the very end.

16. **1965 Ford Mustang**: The 1965 Ford Mustang holds a special place in automotive history as a symbol of freedom and rebellion. Sinatra’s relationship with this car is emblematic of his multifaceted personality as he embraced the spirit of American culture in the 1960s. The Mustang not only represented a shift in car design but also aligned perfectly with Sinatra’s own reinvention as an artist during this vibrant era, showcasing his ability to connect with the evolving landscape of American music and lifestyle.

17. **1947 Cadillac Series 62**: Sinatra’s love for Cadillacs began early in his career, and the 1947 Cadillac Series 62 was one of the first vehicles he owned. This car was known for its smooth ride and elegant styling, embodying the post-war optimism of the time. Sinatra’s choice of this model reflected his rising fame as a musician and his appreciation for craftsmanship, setting the stage for his later automotive acquisitions.

File:1959 Pontiac Bonneville Convertible (36279727136).jpg – Wikimedia Commons, Photo by wikimedia.org, is licensed under CC BY 2.0

Each of these vehicles tells a story that reflects Frank Sinatra’s life, his extraordinary career, and his undying passion for cars. From the glitz of the Cadillac Eldorado to the practical charm of the Chrysler LeBaron, Sinatra’s collection is a vivid testament to his impeccable taste and love for innovation in the automotive world. As we gaze back at these iconic rides, we not only appreciate the craftsmanship behind them but also the memories they encapsulate, showcasing that Sinatra’s legacy is as much about the music he created as it is about the style he embodied through his collection of cars.