Frank Sinatra’s cars reveal more about him than his music ever did. Behind the wheel, he showed his true character without singing a single note. His progression from American luxury to European sports cars mapped his journey from local talent to global icon. The collection featured both gifts from fellow celebrities and custom-designed statement pieces.
Step inside these legendary vehicles to understand the real man behind the microphone.
9. 1955 Ford Thunderbird: A Symbol of Success
Capitol Records celebrated Sinatra’s meteoric rise by gifting this stunning ’55 Thunderbird. Chrome grille, distinctive fog lamps, and hooded headlights defined its elegant profile. Capable of reaching 112 mph, this sporty two-seater delivered serious performance in a stylish package. Originally retailing for under $3,000, the Thunderbird offered tremendous value, though Sinatra’s association made it priceless. Its classically styled yet thoroughly modern character mirrored Sinatra’s own public persona.
1955 Ford Thunderbird: A Symbol of Success (Interior)
Drivers seeking both luxury and sporting character found exactly that in the T-Bird’s cockpit. Aircraft-inspired gauges and easily reached controls emphasized driver engagement rather than passive comfort. The layout mirrored Sinatra’s public image—sophisticated yet approachable, premium without pretension. Standard leather seating and the tach-equipped dashboard appealed to his appreciation for quality craftsmanship and functional design, striking the perfect balance between luxury and sportiness. If you like this, take a look at Will Smith’s car collection.
8. 1956 Continental Mark II: The Height of Luxury
Mid-century automotive luxury reached its zenith in the 1956 Continental Mark II. The Rat Pack’s undisputed leader naturally gravitated to a car matching his elevated status. Each unit underwent rigorous quality control after being hand-built with meticulous attention to detail. An upright spare wheel cover on the trunk became the car’s signature styling element. The 368 cubic-inch V8 delivered 285 horsepower, balancing elegance with substantial performance—much like Sinatra himself.
1956 Continental Mark II: The Height of Luxury (Interior)
Supple Scottish leather crafted with old-world precision greeted anyone entering Sinatra’s Continental. Every switch and surface received the same exacting standards as the exterior, with hand-finished details throughout. The spacious cabin accommodated both driver comfort and passenger luxury—ideal for a star accustomed to taking the wheel and being chauffeured. No mass production shortcuts appeared anywhere in the cabin, reflecting Sinatra’s appreciation for uncompromising craftsmanship.
7. 1958 Cadillac Eldorado Brougham: Flamboyance on Wheels
Vegas strip cruising demanded the flamboyance of a 1958 Cadillac Eldorado Brougham. Revolutionary self-leveling air suspension maintained ride quality regardless of passenger load or road conditions. Sinatra’s collection included several examples, notably a striking burgundy model that commanded attention. The pillarless hardtop design created an open, airy profile perfectly suited to his larger-than-life persona while maintaining the dignified presence expected of a true star.
1958 Cadillac Eldorado Brougham: Flamboyance on Wheels (Interior)
Luxury innovations abounded inside the Eldorado Brougham. Power seats with memory settings—revolutionary for 1958—complemented electric windows, automatic climate control, and cruise control. Sinatra’s burgundy example featured gray and cream leather upholstery with meticulous stitching. Even the glovebox offered luxury, housing a complete vanity set with shot glasses—perfect for impromptu celebrations. This blend of technology and thoughtful details created the ultimate Rat Pack cruiser.
6. 1969 Lamborghini Miura: Sinatra’s Supercar
Automotive history changed forever with the 1969 Lamborghini Miura‘s revolutionary mid-engine layout. Sinatra’s Miura S version extracted 370 horsepower from its 3,929cc V12, achieving a staggering 174 mph top speed. The distinctive arano metallico (orange) paint highlighted its pop-up headlights and perfect proportions. His choice demonstrated appreciation for automotive innovation and boundary-pushing design—qualities that mirrored his own artistic approach.
1969 Lamborghini Miura: Sinatra’s Supercar (Interior)
Rare Bor skin leather wrapped the driver-focused cockpit of Sinatra’s Miura. Controls angled toward the pilot, emphasizing the race-inspired DNA while maintaining minimal grand touring comfort. Despite notorious cabin heat from the V12 engine positioned directly behind the seats, Sinatra embraced this imperfection for the car’s extraordinary performance. This balanced approach to luxury and functionality paralleled his own artistic philosophy of accepting minor compromises to achieve greatness.
5. 1970 Maserati Ghibli: Elegant Italian Style
Italian design evolution continued with Sinatra’s 1970 Maserati Ghibli, acquired four years after his Miura. The 288 cubic-inch V8 generated over 300 horsepower, reaching 154 mph with greater refinement than his Lamborghini. Silver paintwork with tasteful chrome trim presented a more understated profile while maintaining presence. Flowing lines revealed subtle influences from both the Thunderbird and Dual Ghia. His son-in-law handled the purchase, highlighting how Sinatra’s automotive passion extended throughout his family.
1970 Maserati Ghibli: Elegant Italian Style (Interior)
Sophisticated black leather upholstery created an elegant environment inside the silver Ghibli. More practical space than the Miura came without sacrificing sporting character. Classic analog gauges emphasized readability over flash—reflecting Sinatra’s maturing tastes. Actor George Hamilton later owned this very car, maintaining its celebrity provenance. The thoughtfully balanced interior design made it equally suitable for spirited driving and comfortable long-distance travel.
4. 1976 Jaguar XJS V12: A Gift of Power and Elegance
Marriage to Barbara Marx brought Sinatra the 1976 Jaguar XJS V12 as a wedding gift. Following the legendary E-Type, the XJS maintained performance while adding grand touring comfort. Its V12 engine enabled 150 mph with 0-60 acceleration in 7.8 seconds—impressive during the mid-70s performance decline. Distinctive flying buttress C-pillars created a profile unlike anything in his previous collection. Keeping this gift for 19 years demonstrated his appreciation for both the car and his relationship with Barbara.
1976 Jaguar XJS V12: A Gift of Power and Elegance (Interior)
British luxury traditions defined the XJS interior with rich leather, polished wood, and that distinctive Jaguar cabin ambiance. Sinatra upgraded his with a high-end Panasonic radio and early car phone technology. The 2+2 seating configuration accommodated occasional passengers while maintaining an intimate sporting GT feel. Despite representing a departure from his usual automotive preferences, the XJS clearly satisfied his requirements throughout nearly two decades of ownership.
3. 1981 Chrysler Imperial FS Edition: A Lifelong Loyalty Rewarded
Brand loyalty culminated in the 1981 Chrysler Imperial FS Edition bearing Sinatra’s initials. Built on the 112.7-inch wheelbase Cordoba platform, it featured distinctive “bustleback” styling similar to the Cadillac Seville. Limited production included just 278 units across 1981-1982, many in Glacier Blue Crystal matching Sinatra’s famous eyes. Initially the most expensive American car at $20,000-$25,000, it featured a crystal Pentastar hood ornament by Cartier. Sinatra personally drove the first production model off the assembly line.
1981 Chrysler Imperial FS Edition: A Lifelong Loyalty Rewarded (Interior)
Premium Mark Cross leather and genuine wood trim elevated the Imperial’s interior. A special console housed 10 Frank Sinatra cassette tapes in each vehicle. Chrysler’s 318 cubic inch (5.2L) V8 with electronic fuel injection—the company’s first—powered the FS Edition, though these systems often required replacement with carburetors due to reliability issues. Despite 14-15 MPG fuel economy and susceptibility to deck lid rust, the FS Edition created a unique automotive-celebrity partnership that collectors increasingly value today.
2. 1984 Rolls-Royce Corniche: A Gift from the Rat Pack
Sinatra’s 70th birthday brought the gift of a 1984 Rolls-Royce Corniche from Rat Pack members Sammy Davis Jr. and Dean Martin. Finished in Mason black, this handcrafted British convertible epitomized timeless elegance. The fuel-injected V8 could reach 120 mph, while the power-operated top, Spirit of Ecstasy hood ornament, and hand-painted coachlines created the ultimate luxury statement. Later gifting it to assistant Igar Frederickson demonstrated that Sinatra’s generosity matched his exceptional automotive taste.
1984 Rolls-Royce Corniche: A Gift from the Rat Pack (Interior)
Hand-stitched burgundy leather surrounded occupants in the Corniche’s sumptuous interior. Fold-down picnic tables, crystal glasses, and decanters transformed the rear seating area into a mobile lounge. The Connolly leather required two weeks to hand-cut and stitch for each Corniche. Burled walnut dashboard and lamb’s wool carpets represented the pinnacle of British craftsmanship. Every material, comfort feature, and detail reinforced why the Corniche deserved a place among Sinatra’s automotive collection.
1. 1985 Chrysler Town & Country: A Modest End
Full-circle automotive evolution arrived with the 1985 Chrysler Town & Country wagon. Reportedly the last car Sinatra personally drove, this practical station wagon showed his eventual prioritization of comfort and utility. The 3.6L V6 engine produced 283 horsepower—impressive for a family vehicle of that era. Clean lines and wagion practicality revealed Sinatra’s willingness to choose function over flash in later years, perhaps the most authentic expression of his automotive philosophy.
1985 Chrysler Town & Country: A Modest End (Interior)
Comfort superseded luxury inside Sinatra’s Town & Country. The spacious interior facilitated easy entry and exit—increasingly important for the aging entertainer. Though lacking exotic materials from his earlier cars, the wagon delivered excellent ride quality and thoughtful ergonomics. Straightforward controls and clear instrumentation created an ideal daily driver without unnecessary complications. This final chapter demonstrates how true automotive appreciation transcends flash and status, ultimately focusing on finding the right tool for life’s journey.
