Four of the most outrageous fins in automotive history will go under the hammer at Shannons' Sydney Summer auction on Monday February 12. They're on two 1959 Cadillacs, a Series 60 Special Fleetwood pillarless sedan and matching Series 6200 Convertible. They were each converted to right-hand drive and fully restored at great expense in 2000 and according to Shannons, are in "better than new" condition. The 1959 Cadillac makred the pinnacle of the Ameriac love affair with fins that had started on late 1940s Cadillacs. The fins were inspired by the twin fin and rudder assenmbly on the World War 2 Lockheed Lightning fighter place, The 1959 Cadillac Convertible in particular has gone down in history as the automotive equivalents of Marilyn Monroe – drop dead gorgeous, totally over the top and never to be repeated. The 1959 Cadillac's fins were the tallest of any production car – each bisected by twin bullet taillights. Under the skin, the 2.2 tonne 1959 Cadillac was powered by a new, vastly improved 390-cid V8 and came with luxury features including power windows, power brakes, power steering, power antenna and six-way power front seat, while the convertible naturally had a power-operated roof that folded away at the touch of a button. The six-passenger Fleetwood was available only as a four-door hardtop and with only 12,250 made out of Cadillac’s total 1959 production of 142,272, was a select and very upmarket model. The 1959 Cadillac Convertible was even rarer and more prestigious. An automotive icon in the true sense of the word, it has inspired countless paintings and sculptures, been immortalised in film and celebrated in numerous industrial design exhibitions around the world. During their restoration, both Cadillacs had their bodies stripped and sandblasted prior to painting, while the fully-documented work saw many mechanical components including the Convertible’s transmission, either reconditioned or replaced. Each was then painted white and re-trimmed with matching white and metallic silver flake vinyl, along with a new dashboard. Both vehicles retain their original in-dash radios to preserve their period appearance, but are fitted with modern CD players and in the case of the Fleetwood pillarless sedan, air conditioning. Other exclusive equipment on the Convertible includes Cadillac’s advanced Autronic-Eye power headlight control and a pearl steering wheel. Said to run like clockwork, the Cadillacs would make perfect summer cruisers that could easily double as a business proposition or wedding cars on weekends. Shannons are expecting bids in the range from $Au45,000-$50,000 for the Series 60 Fleetwood pillarless sedan and $Au110,000-$130,000 for the Convertible.