Olivier Gendebien was born in Brussels, Belgium. His maternal grandmother (Hélène van der Straeten, ne Solvay) was the daughter of Ernest Gaston Joseph Solvay who founded the Belgian Chemical giant Solvay S.A.. He was thus an heir to a substantial fortune (though not descended from aristocracy).
A gifted athlete who once ran the 100 meters in 10.9 seconds, Olivier was studying engineering at university when Germany invaded Belgium at the start of World War II. He joined the resistance movement and being good with languages (he eventually he spoke six fluently) his English (which he credited to his English nanny) helped him act as the liaison with British agents being parachuted in behind enemy lines. He eventually decided to escape to England where he served in a special Belgian Paratroop unit attached to the British army.
When the war ended Gendebien switched to studying agricultural engineering and, after a spell working in Spain, where he went to learn the language, he moved to the Belgian Congo in 1948 to work helping with clearing land for the development of what would become the residential area of Stanleyville. During his four years there he gained a reputation for his speed and ability to control big American cars of the local roads as well as hunting the occasional Buffalo, the horns of one particularly fine beast hung on the wall of his home in Fontainebleau, just outside Paris. He also met Charles Fraikin there. Fraikin owned an XK120 and was looking for a co-driver for when he returned to Europe, which they did together in 1952.
Gendebien's first race was however not with Fraikin. It was actually in the Formula 2 Grand Prix des Frontières at Chimay on June 1st that year. He drove a Veritas RS BMW to seventh place in the race which was won by Paul Frère. He raced the Ecurie Francorchamps Veritas again in August at the Nürburgring and made his debut in the Liège-Rome-Liège rally finishing 22nd with Fraikin in the latter's XK120.
In 1953 he continued to co-drive with Fraikin. They took on the Mille Miglia in April but failed to finish and then had his first outing in a Ferrari driving a Gery d'Hendecourt's 166 MM (0064M) to win the the Coupe de Spa at Spa-Francorchamps on the 17th May. He drove a Dyna Panhard in the Spa 24 Hour race and a C Type Jaguar in the Nürburgring 1000Ks failing to finish both races. Back with Fraikin they finished 8th in the Alpine Rally in July and also competed on the Tour de France in September.
1954 saw a similar mix of races and rallies. His cousin Philippe Washer, one of the most successful players in the history of Belgian tennis, had bought a Ferrari 250 Europa GT which Olivier bought from him. He finished second in class in the Cote de la Roche in March before winning the Tulip Rally in April driving an Alfa Romeo 1900 TI with Pierre Stasse. He then won the GP des Voitures de Série at Spa in May driving d'Hendecourt's 166 MM again. On the Tour de France he finished 7th overall driving with Pierre Stasse in the 250 Europa. He drove with Fraikin again but by now they were getting know as 'the eternal bridesmaids' due to the number of times they finished as runners up. Gendebien also teamed up with Gilberte Thirion and together they finished tenth on the Lyon-Charbonnieres Rally in a Fiat. They took a class win and fourth overall on the Evian Mont Blanc-Megeve Rally driving a Porsche and seventh and another class win on the Tour of Italy driving a Plymouth. They also raced finishing 14th in the Rheims 12 Hour race in a Gordini T15S.
Things moved up a gear in 1955 when he acquired a Mercedes 300SL. In the Mille Miglia he drove with his cousin Jacques Washer to finish 7th overall and second in class. At Le Mans for the first time he finished 5th overall and second in class in a Equipe Nationale Belge entered Porsche 550/4 RS 1500 Spyder with Wolfgang Seidel and he won both the Liège-Rome-Liège Rally and the Coppa d'Oro delle Dolomiti, beating Castellotti's factory entered Ferrari 500 Mondial.
Within a week he had been given a works drive at Marinello and lined up on the 10th July for the 10 Hour race at Messina partnering Umberto Maglioli in a 750 Monza. A week later he took a class win and second overall in the Aosta-Gran San Bernardo Hillclimb driving a 500 Mondial S.II but then crashed in practice for the RAC Tourist Trophy at Dundrod putting an end to his season.
He had done enough to keep his place as a work driver for Ferrari and lined up on the grid in Buenos Aires for the first F1 race of 1956 the Argentine Grand Prix. It was an impressive debut and he finished 5th in the Lancia-Ferrari D50. Still in Argentina he partnered Phil Hill in the 1000Km race taking a class win and second overall. He also drove in the non-championship Buenos Aires GP at Mendoza finishing 6th.
Back in Europe in March he was second at the La Roche Hillclimb before taking class wins in the Giro di Sicilia and the Mille Miglia with his cousin in a 250 GT LWB Berlinetta Scaglietti 'Tour de France'. He drove with De Portago in the 1000Km race at the Nürburgring but they were disqualified for receiving outside assistance. They then took over the Hill/Wharton car, bringing it home in 3rd place.
Gendebien continued to put in some great drives in sportscars and after another class win in the Coppa d’Oro delle Dolomiti in early July he finished 3rd overall and 1st in class at Le Mans. he also finished 3rd in the Liège-Rome-Liège and the Tour de France.
His only other F1 appearance that year was in the French Grand Prix in July when retired when his clutch failed on lap 38.
He didn't make any F1 appearances in 1957 but in sportscars he had a great year winning the Giro di Sicilia outright and taking a class win and 3rd overall in Mille Miglia. He was second with Phil Collins in the Nürburgring 1000Ks before winning the Reims 12 Hour race with Paul Frere. A win in the Tour de France and the Coupes du Salon at Montlhery as well as a class win in the Nassau Tourist Trophy during Speed Week rounded out his year.
1958 saw him finish second at Sebring and then take outright wins at Pau in the 3 Hour race, the Targa Florio, Le Mans, the 12 Hour race at Reims and the Tour de France. In F1 he finished 6th in his home Grand Prix but retired in his two other appearances that year.
By 1959 he had started to scale back his racing choosing to concentrate on major races. He partnered Dan Gurney, Chuck Daigh and Phil Hill to win at Sebring again. He also won the GT Paris Grand Prix at Montlhery and, partnered with Bianchi, he took his third Tour de France. he had only two Formula One drives, and though he finished in the points with a 4th in France and a 6th in Italy there was little chance of ever getting a full season at the top level.
Now 36 years old his chances of F1 glory were fading. So in 1960 he mounted a serious assault in the sports premier division. Driving the Yeoman Credit Racing Team's Cooper-Climax. He finished third in the Belgian Grand Prix and second in the French Grand Prix. He also raced in the British, Portuguese and American Grand Prix. He also raced in a number of Formula Two races and drove sports cars for Porsche. Teamed with Hans Hermann, they won Sebring and took third in the Targa Florio driving a Porsche 718 RS 60 and partnering Jo Bonnier he was second at the Nürburgring again in a Porsche 718 RS 60.
Le Mans was a critical race for Ferrari that year as a in would give them the sports car championship over Porsche. Gendebien was thus re-hired by Ferrari for the long distance classic. Paired with Paul Frere he gave Marinello what they were looking for and duly won his second Le Mans. The win was due in no small part to his driving style as two of the four works cars ran out of fuel before the first round of pit stops! he also won the Paris 1000 Km at the end of the year.
Gendebien was back with Ferrari in 1961 mainly to drive sports cars. He won at Sebring with Phil Hill and the Targa Florio with Von Trips. He was due to race with Hill but was unsure of the car they had been given. He thus left it to Hill to start as he had no intention of being stranded out on the circuit. He was partially right as Hill crashed out. Gendebien took over Richie Ginther's seat in the 246 SP0.
At the Nürburgring, Maserati took the win with Gendebien and von Tripps only managing 3rd but at Le Mans he was back with Hill and they took their second (Gendebien's third) victory. His made one start for Ferrari in Formula One in his home Grand Prix driving a yellow 156 to fourth place in Ferrari's clean sweep of the first four places.
He further reduced his racing in 1962 partially from family pressures as he now had three children. He finished second at Sebring (1st in GT) marking the debut of the Ferrari 250 GTO. he then took three straight victories in the Targa Florio, Nürburgring 1000 km and his fourth win at Le Mans. It must have seemed like the right time as he announced his retirement. "Racing" he said "didn't amuse me so much any more." he went on to say "there seemed only two choices, one to die, the other one to lose. I decided on a third one. To stay alive."
Nicknamed 'L'écureuil' (The squirrel) for his ability to get into his car quickly during the Le Mans style starts he was one of the greatest long distance sports car drivers ever. Considered by some to be cold and arrogant at times, he never enjoyed the popular support that some of his piers did and he didn't have the best of relationships with the press either. However Enzo Ferrari once said of him that he was "a gentleman who never forgets that noblesse oblige and, when he is at the wheel, he translates this code of behaviour into an elegant and discerning forcefulness."