Annett began racing after high school, starting at Hawkeye Downs in Iowa and progressing to the American Speed Association series. Prior to his racing career, Annett played defense for the Waterloo Black Hawks of the United States Hockey League. He was a member of the team that won the Clark Cup in 2004 and was named “Most Improved Player” on a team that included future NHL player Joe Pavelski. His father previously owned a dirt track team that fielded drivers including Sammy Swindell. At 5 ft 10 in (1.78 m), and 180 lb (82 kg), he was considered too small to play at a higher level.
Annett competed in a handful of NASCAR Craftsman Truck Series events in 2008, with a best finish of second at Kentucky Speedway. He returned to the series on two occasions, in 2014 at Eldora Speedway with NTS Motorsports, and in 2021 at Knoxville Raceway for Young's Motorsports. He was replaced by Chris Windom at Knoxville after practice due to a leg injury.
Towards the end of 2008, Annett signed with Germain Racing to drive in NASCAR’s Nationwide Series, debuting at Homestead-Miami Speedway where he finished 36th after a crash. In 2009, Annett ran for Rookie of the Year in the No. 15 Toyota Camry, sponsored by Pilot Travel Centers and HYPE Energy, scoring four top-ten finishes and finishing tenth in points. He returned to Germain in 2010, earning two top-tens at Nashville and Iowa, and finishing thirteenth in the overall points standings.
Annett moved to Rusty Wallace Racing in 2011, achieving seven top-ten finishes and placing ninth overall in points. In 2012, driving for Richard Petty Motorsports, he earned six top-fives and seventeen top-tens, finishing fifth in points.
The 2013 season saw Annett suffer a hard crash in the season-opening DRIVE4COPD 300 at Daytona International Speedway, initially diagnosed with a bruised sternum. Further evaluation revealed a dislocation and fracture requiring surgery, and he was replaced by Aric Almirola and Reed Sorenson during his recovery. He returned in Charlotte in May, recording one top-five and four top-tens, finishing fifteenth in the points standings.
On November 4, 2016, Annett announced he would be returning to the Nationwide Series – now known as the Xfinity Series – in 2017, driving the No. 5 Chevrolet Camaro for JR Motorsports on a full-time basis. In his first full-time season with JRM, he scored one top-five and seven top-tens, finishing ninth in points. In 2018, he had three Top 10 finishes, finishing fourteenth in points. On January 25, 2019, it was announced that Annett would be driving the No. 1 Chevrolet, with the points from the No. 5 car transferring to the No. 1 car.
On February 16, 2019, Annett scored his first and only career victory in the NASCAR Racing Experience 300 at Daytona International Speedway. He credited crew chief Travis Mack, who joined the team in late summer 2018, as a catalyst for the success. Annett returned to JRM in 2020 and qualified for the playoffs, being eliminated after the first round.
In July 2021, Annett missed races at Atlanta and New Hampshire due to a stress fracture in his right femur, with Austin Dillon and Josh Berry substituting. After the race at Watkins Glen, Chase Elliott replaced him at Indianapolis, and Josh Berry also substituted at Michigan. He reinjured his right femur after Michigan, missing races at Bristol, Las Vegas, and Talladega, with Josh Berry again filling in. On October 6, 2021, Annett announced he would retire from full-time competition at the end of the season.
In November 2013, Annett moved up to the NASCAR Sprint Cup Series for the 2014 season, driving for Tommy Baldwin Racing. It was a difficult rookie season with only four top-twenty finishes. Annett announced on January 27 that he was switching teams to HScott Motorsports, bringing the team to a two-car operation. He qualified for the Daytona 500, finishing thirteenth. He failed to qualify at Atlanta but was given a spot by Richard Childress Racing development driver Brian Scott, who was running for Xfinity Series points. He later failed to qualify at Talladega. At the end of the 2015 season, his average finish was worse with HScott Motorsports than with Baldwin. Annett was replaced by Justin Allgaier prior to the Bass Pro Shops NRA Night Race due to flu-like symptoms and announced on November 1, that he would not return to HScott Motorsports in 2017.
On February 6, 2011, Annett was involved in a traffic accident in Mooresville, North Carolina, rear-ending a car stopped at a red light. Police reports indicated a BAC of 0.32, four times the legal limit in North Carolina. He resisted arrest and admitted to texting while driving, with a similar incident occurring in 2010. Rusty Wallace Racing issued internal sanctions, and NASCAR remained in contact with local authorities. Annett issued a formal apology and did not miss any races.
Annett died on December 2, 2025, with the announcement coming from JR Motorsports and NASCAR on December 5.
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