Nannini was born in Siena on 7 July 1959. He began racing in a Lancia Stratos at national rally events before switching to Formula Italia in 1981. From 1982 to 1984 he raced for Minardi in Formula Two. Although his best championship season saw him finish only seventh overall in 1983, his speed attracted attention despite uncompetitive machinery.
During this period Nannini was also signed by Lancia to drive their LC2 prototype in the World Sportscar Championship. He set the fastest lap at the 1984 24 Hours of Le Mans while battling for the race lead with the Kremer Racing Porsche 956 of 1980 F1 World Champion Alan Jones about four hours after the start, finishing eighth alongside Frenchman Bob Wollek. Later in 1984 he won the 1000 km of Kyalami alongside Riccardo Patrese.
For 1985, Nannini was Giancarlo Minardi's first choice for the team's inaugural Formula One entry, but he was controversially denied a Super Licence by FISA, with former F2 teammate Pierluigi Martini taking the drive instead. Nannini continued with Lancia in the 1985 World Sportscar Championship, finishing eighth in the Drivers' Championship with third-place finishes at Monza and Silverstone, both times paired with Patrese.
In 1986 Nannini was finally granted a Super Licence and joined Minardi's Grand Prix team, where he stayed through 1987. The Motori Moderni V6 engine was disappointing; he was classified in only four of 30 starts. Despite this, his raw speed was widely noted, particularly after he largely outperformed the more experienced Andrea de Cesaris in 1986 — to the point where de Cesaris would demand to have Nannini's car if his younger teammate was faster than him. In 1987, in his spare time, Nannini won the Mille Miglia alongside veteran road-race driver Giorgio Marin.
Benetton signed Nannini for 1988 to partner Thierry Boutsen. He generally performed very well, often out-pacing the highly regarded Belgian. He scored his first championship point in his second race for the team, took two third-place finishes, and ended the year tenth in the championship.
With Boutsen leaving for Williams for 1989, Nannini was joined by young Englishman Johnny Herbert. He achieved podiums at the British and Spanish Grands Prix. At Suzuka, Nannini was running third behind Senna and Alain Prost when the two McLarens collided. Nannini took the lead; Senna rejoined after being push-started, pitted to replace his front wing, then caught and passed Nannini before crossing the line first. Senna was subsequently disqualified for missing the chicane following the collision, handing the victory to Nannini. He rounded off 1989 with a second-place finish in torrential rain at Adelaide, moving him to sixth in the championship.
For 1990 Nannini was joined by triple World Champion Nelson Piquet. He largely matched Piquet's pace throughout the season. At the German Grand Prix at Hockenheim, Nannini led for 16 laps on a non-stop tyre strategy, his Benetton-Ford V8 resisting the more powerful McLaren-Honda V10 of Senna before fading grip dropped him to second. At the Hungarian Grand Prix he hounded leader Thierry Boutsen until Senna controversially pushed him off the track and into retirement. He finished third at the Spanish Grand Prix the following round.
On 12 October 1990 — one week after the Spanish Grand Prix — Nannini was involved in a helicopter crash at his Siena vineyard when the ground beneath the landing helicopter gave way. Nannini suffered a severed right forearm. Microsurgery successfully reattached the limb, but the injury ended his Formula One career. At the time of the accident he had been reconfirmed by Benetton for 1991; Ferrari had a long-standing interest in him and McLaren boss Ron Dennis had also been keeping an eye on him.
In 1992, Ferrari offered Nannini a test drive at the private Fiorano Circuit. He completed 38 laps in Jean Alesi's Ferrari F92A, which featured a specially modified steering wheel. In 1996, Benetton's Flavio Briatore honoured a promise of a test drive, which took place at Estoril in a B196.
Despite regaining only partial use of his right hand, Nannini resumed professional racing with Alfa Corse in the Deutsche Tourenwagen Meisterschaft from 1993. He finished fourth overall in the 1994 DTM championship and third in the 1996 International Touring Car Championship. In 1997 he competed for Mercedes in the FIA GT Championship, winning a race at Suzuka and finishing sixth overall before retiring. He returned briefly to competition in 2007 for the Grand Prix Masters series, which included former Benetton teammate Johnny Herbert.
Nannini runs a chain of upmarket cafes bearing his name, with branches as far afield as Indonesia. He is a member of the Italy–USA Foundation. Matteo Nannini — son of a first cousin of Alessandro — is also a racing driver, having competed in Formula 3 and Indy NXT.
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