Annett’s first love was ice hockey, and he advanced quickly through the developmental ranks. By the time he was 16 years old, Annett was playing for Team Illinois, a Triple-A hockey team. In 2004, the Hawkeye native joined the Waterloo (Iowa) Black Hawks, a United States Hockey League (USHL) team. He was awarded the USHL Most Improved Player award in 2004. Due in part to his father Harrold Annett’s background as team owner for sprint car legend Sammy Swindell, Annett found the siren song of motorsports too strong to ignore. In 2005, Annett made a full-time transition into the racing world and traded his skates for a fire suit.
 
The Des Moines, Iowa native began his racing career in 2007, competing in the ARCA Racing Series where he found instant success. Annett won the pole for his first ARCA race at Iowa Speedway, his home track. In just 10 ARCA races from 2007 to 2009, Annett amassed two wins (Talladega, Daytona), five top-five and eight top-10 finishes.


In 2008, Bill Davis Racing and Germain Racing gave Annett the opportunity to gain seat time in the Truck and Xfinity Series. From 2009 through 2013, Annett raced full-time in NXS competition with multiple teams including Germain Racing (2009-10), Rusty Wallace Inc. (2011), and Richard Petty Motorsports (2012-13). Before making the jump to the Cup Series, Annett collected seven top-five and 34 top-10 finishes in NXS competition. His most successful year in NXS to that point came in 2012, where he earned six top-five and 17 top-10 finishes en route to a fifth-place effort in the championship standings.
 
Following a three-year stint (2014-16) at the NASCAR Cup Series level, driving the No. 7 for Tommy Baldwin Racing and the No. 46 for HScott Motorsports, Annett joined JR Motorsports in the NASCAR Xfinity Series.
 
Driving the No. 1 made famous by Sammy Swindell at the dirt level, Annett spent five years behind the wheel of the Dale Earnhardt, Jr.-owned Chevrolet, earning 61 top-10s, 12 top 
5-s, 1 pole, and a win at Daytona International Speedway in the 2019 season opener.
 
Annett announced his retirement from full-time competition in late 2021, bookending a
14-year career at the top levels of NASCAR.