Born in Norwalk, Connecticut, Sharp began racing karts at age eight, winning fifty out of 75 races. He earned championships in the 1986 SCCA GT-2, 1987 and 1988 SCCA GT-1, and 1991 and 1993 SCCA Trans-Am classes. He competed in one NASCAR Winston Cup Series event in 1992 at Watkins Glen. In 1993 Sharp made his CART debut with Bettenhausen Motorsports and became a full-time CART competitor in 1994 with PacWest Racing. His first Indianapolis 500 start came in 1994. In 1996 Sharp was part of Doyle Racing's 24 Hours of Daytona winning team.
Sharp was a competitor in the first IRL race in 1996, driving for A. J. Foyt Enterprises. He was the co-champion of the IRL's inaugural season in 1996 along with Buzz Calkins.
In 1997, two crashes resulting in severe concussions sidelined Sharp until 1998, when he began working with the newly formed Kelley Racing team and sponsor Delphi. At Kelley, Sharp collected eight wins and four pole positions, including one at the 2001 Indianapolis 500. He was third in the championship in 2001. In 2004 — his first winless season since 1998 — he finished thirteenth in the championship, ending a run of top-eight championship finishes dating back to 1998.
Kelley Racing folded after 2004. In 2005, Sharp and Delphi moved to Fernández Racing; Sharp finished fifth in the championship that season and collected a win at Kentucky Speedway. He struggled through 2006 with the team adapting to the Dallara chassis, finishing eleventh in points.
For 2007 Sharp joined Rahal Letterman Racing, teaming with sophomore driver Jeff Simmons before Simmons was replaced mid-season by Ryan Hunter-Reay. Sharp brought primary sponsor the Patrón Spirits Company, ending nine seasons of backing from Delphi. His best finish of 2007 was third, earned at the season opener at Iowa Speedway and at Michigan International Speedway. He took a surprise pole position at Texas Motor Speedway in June — his first pole since 2001 — and recorded a career-best sixth place at the Indianapolis 500. He ended 2007 eighth in the championship.
Sharp is one of only two drivers — the other being Buddy Lazier — to have driven in at least one race in each of the first twelve seasons of IndyCar competition (1996 to 2008). His IRL records for that era include: most career IndyCar Series starts (147), most consecutive IndyCar Series race starts (138), and most races running at finish (110). He previously held the records for most top-ten finishes (82) and most consecutive seasons with at least one race win (seven), since broken by Hélio Castroneves.
Sharp returned to the series and competed in the 2009 Indianapolis 500 with Panther Racing, qualifying twentieth and finishing fourteenth on the lead lap.
Sharp and Patrón joined the American Le Mans Series with Highcroft Racing for 2008, driving the No. 9 Patrón Highcroft Racing Acura ARX-01b with David Brabham in the LMP2 class.
Sharp started seventh and finished fourth in class at his debut at the Mobil 1 Twelve Hours of Sebring. The team finished second at the Acura Sports Car Challenge of St. Petersburg. Sharp earned his first ALMS win in the P2 class at Long Beach. He earned his first overall ALMS win at the 2008 Northeast Grand Prix at Lime Rock Park after starting from the pole. A third class victory followed at the Generac 500 at Road America. When leader Gil de Ferran ran out of fuel on the last lap at Mosport, the team collected a fourth victory. SPEEDtv.com awarded Sharp "Drive of the Race" at the Detroit Sportscar Challenge presented by Bosch, though the team settled for second place. Sharp and Brabham were joined by Dario Franchitti for the 10-hour Petit Le Mans; broken suspension took the car out early. The duo finished second in the P2 point standings, forty-one points behind the Penske Racing duo of Timo Bernhard and Romain Dumas, after being as close as four points behind with two rounds to go.
It was announced on the American Le Mans Series website that Sharp would race in the 2010 series under his own team, Extreme Speed Motorsports. He ran with two Ferrari F430s in the GT class, sponsored by the Patrón Spirits Company, alongside Patrón CEO Ed Brown.
In 2011 the team switched to Ferrari 458 Italia GT2 cars and made steady progress, culminating in a third-place finish at Laguna Seca. In 2012 the No. 02 car picked up another podium at Long Beach and the No. 01 won the Grand Prix of Mosport, the team's first win since its move to the GT class. In 2016 Sharp won the Rolex 24 for the second time, this time with ESM.
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