Vintage and classic cars of the stars

Frank Sinatra was the first owner of this 1958 Eldorado Brougham. When Ol' Blue Eyes stumped up what was then an extravagant $13,074 he got every accessory known to Detroit, including a combination lady’s vanity and cigarette case and a set of magnetic shot glasses in the glove box. Estimated to fetch $275,000-$325,000 Photograph: Bonhams/Bonhams

This 1930 Cadillac once belonged to Chicago gangster Al Capone. He had it customised to suit his lifestyle: its doors are reinforced with ¼" steel armour and the glass is bulletproof five-ply laminated. The side windows have round ports cut in them which, auctioneer Bonhams says darkly, are "not for ventilation". Capone was indicted in 1931 so the car remains in near pristine condition. Estimated to fetch $250,000-$300,000 Photograph: Bonhams/Bonhams

This 1955 Alfa Romeo 1900C Super Sprint Berlinetta has been described as "an amazing combination of speed, style, elegance and practicality". It was designed by Orazio Satta Puliga following a systematic evaluation of vehicle dynamics directed at minimizing mass and aerodynamic resistance, and maximizing roadholding and handling. Estimated to fetch $400,000-$500,000 Photograph: Bonhams/Bonhams

When the 32nd president of the United States, Franklin D. Roosevelt, toured California during his second re-election campaign, he did so in this 1935 Lincoln Model K V-12 Phaeton. Perhaps he relaxed making use of the foot rest and smoker's kit fitted for the rear seats. Estimated to fetch $300,000-$350,000 Photograph: Bonhams/Bonhams

This Auto Union D-Type was driven to placing finishes in the 1939 grand prix season and boasts a three-litre, twin-stage supercharged V12-cylinder engine. It is the only individually-identifiable complete original grand prix race team chassis frame known to have survived from that season. Estimated to fetch $8m Photograph: Bonhams/Bonhams

This is the 1934 Rolls Royce Phantom II Touring Saloon, the last Rolls designed under F. Henry Royce, co-founder of the great marque. It was powered by a massive 7.7 litre, six-cylinder engine. It underwent a thorough restoration in the early 1980s. Estimated to fetch $150,000-$200,000 Photograph: Bonhams/Bonhams

This is a 1933 Duesenberg Model J Torpedo Victoria Convertible, first owned by cinema cowboy William Boyd – Hopalong Cassidy to you and me, the hero of 66 immensely popular films. With a mechanically operated folding top this is a fine example of open coachwork on the majestic Duesenberg Model J chassis. Estimated to fetch $1.2m-$1.6m Photograph: Bonhams/Bonhams

Inspired by the racing D-Type, this 1964 Jaguar XK-E Custom Roadster was a radical shift of the XK idiom that had proved so successful in the 1950s. It adopted independent rear suspension and was equipped with inboard disk brakes. Handling was aided by front and rear anti-roll bars. Estimated to fetch $75,000-$100,000 Photograph: Bonhams/Bonhams

The Mercedes Benz 300SL Coupe was introduced in 1954 as a two-seat, closed sports car with distinctive gull wing doors. It was the fastest production car of its time capable of speeds of up to 161mph. Low production numbers and a famous previous owner – Clark Gable – should ensure a high price. Estimated to fetch $500,000-$600,000 Photograph: Bonhams/Bonhams

This 1962 Ghia 6.4L Coupe was owned by Gary Morton (Lucille Ball’s second husband) and later modified for its second owner, Dean Martin, by the King of the Kustomizers, George Barris. Estimated to fetch $185,000-$225,000 Photograph: Bonhams/Bonhams

This 1952 Siata 208 CS Berlinetta is an ultra rare Italian racer, regarded as one of the most brilliant designs ever created by the marque. It was built for the 1952 Turin Auto Show and the Italian open road endurance race the Mille Miglia. Estimated to fetch $1.6m-$1.9m Photograph: Bonhams/Bonhams