Two of the greatest boxers of all time who were active in the 1920s were Jack Dempsey and Gene Tunney. Other noteworthy pugilists of the time include Panama Al Brown, Harry Greb, Benny Leonard and Jimmy Wilde.

Boxing entered its heyday as a sport during the 1920s, and the best boxers enjoyed the limelight alongside baseball players, movie stars and politicians. Boxing became legitimized during this time after the creation of the National Boxing Association, which sanctioned fights, listed rankings and attempted to keep corruption to a minimum.

William "Jack" Harrison Dempsey was the sport's biggest star, and fought some of boxing most famous fights during the 1920s, including fights with Luis Firpo and a pair with Tunney. In 1921, he and Georges Carpentier fought in the sports first-ever million dollar fight. With his success, Dempsey ended up a household name, eventually dating Hollywood starlets and becoming a successful restauranteur.

Tunney was more low-key, but maybe even a better boxer than Dempsey. Tunney defeated Dempsey in 1926, ending Dempsey's 7-year reign as the titleholder. For good measure, Tunney defeated Dempsey again in the rematch a year later in a bout that became known as "The Long Count Fight." This stems from when Tunney knocked Dempsey down in the eighth round and the referee started counting Dempsey out before Tunney moved to a neutral corner. Dempsey survived the knockdown, but lost the fight in a unanimous decision.