Bennett grew up in Wisconsin, where his father Albert — a beekeeper by trade — raced motorcycles at county fairgrounds across the state during the 1940s. As a child Bennett spotted a Whizzer brand motorcycle in a newspaper advertisement and persuaded his father and grandfather to help him buy it. He took a motorcycle to Rib Mountain near Wausau and prepared it for racing, stripping the fenders and headlights; he dates his racing debut to 1952, when he was a junior in high school.
After graduating he worked as a storage tank welder, travelling the country on the trade before being drafted into the Army. He was stationed in Germany, where he purchased an Austin-Healey and competed in races and hill climbing events against officers. On returning to the United States he bought a 1937 Plymouth as his first stock car and began racing in 1959 at tracks in Oshkosh, Shiocton, Seymour, and De Pere. He was a welder at Valley Iron Works earning $85 a week, and could earn $35 a night racing a stock car two or three evenings a week.
Bennett competed in coupes and late model stock cars across Wisconsin throughout the 1960s and 1970s. He also raced on the USAC and IMCA circuits between 1964 and 1966, running events in Indiana, Illinois, and Kansas. On those circuits he competed alongside A.J. Foyt and Parnelli Jones. Bennett's principal mount on the national circuits was a Hemi-powered Dodge No. 48 equipped with two carburettors, which he estimated produced around 675 horsepower; he noted the car was particularly fast on wet tracks.
His most prominent car in later years was a 1970 Chevelle formerly raced by Jerry "Medina" Smith. Bennett won a 50-lap feature at Shawano Speedway in the mid-1970s against drivers from a three-state area, earning $550 in a result he considered one of his biggest accomplishments. He also won the Fox Valley track title — combining points from several area dirt and asphalt tracks — in 1972. In December 1968 Bennett suffered a plane crash while spotting for a fox hunt, sustaining fractures at 210 different points across his pelvis, chest, legs, and arms; he was back racing the following April, winning his first race after the crash. Over his career across all forms of racing, including heat wins, consolation events, and main events, Bennett estimated approximately 5,000 victories and competition at around 257 different tracks.
Bennett served as president of the Wolf River Racing Association in its inaugural year of 1960, with Roger Paul as secretary and Cliff "Squeak" Miller as treasurer. The association was formed after several drivers had been black-flagged at Fox River Racing Club-run tracks; it sought to establish common rules and race procedures. The WRRA used the Shiocton track as its initial home base and subsequently helped promote races at Shawano.
Among the rules Bennett promoted within the WRRA was a ban on drinking in the pits during events. He also advocated for allowing women into the pit area, a policy he claims made Shawano the first track in the United States to admit women to that section of the venue. The WRRA disbanded when the Shiocton track closed in 1973.
Bennett also co-promoted the weekly programme at Seymour Speedway in 1977 with Tom Hallada; the promotion closed about three-quarters through the season due to insufficient attendance.
Bennett and his wife Patricia had ten children — six sons (Lowell, Brady, Tim, Dave, Aaron, and Joel) and four daughters (Rebecca, Rachel, Becky, and Ruth). Several of his sons raced on dirt and asphalt tracks across Wisconsin in subsequent years.