Head Play (April 2, 1930 – December 11, 1954) was an American Thoroughbred racehorse best known for winning the 1933 Preakness Stakes, the second leg of the U.S.

Trainer Willie Crump, a former top jockey, bought Head Play for $500 at a yearling sale and gave him to his wife Ruth to race under her name.

In his three-year-old season, with jockey Herb Fisher aboard he won the Derby Trial Stakes at one mile at Churchill Downs on opening weekend.

In the time leading up to the race, he began uneasy in the paddock, bucking and exhibiting fractious behavior [4] and was unable to be placed in the stall for saddling.

In May, he ran against the 1934 Kentucky Derby winner, Cavalcade, at Belmont and recorded an upset victory over the younger horse.

[7] On the fourth of July weekend, Head Play won the prestigious Suburban Handicap at 1+1⁄4 miles on the dirt at Belmont Park in New York over Discovery with Cavalcade losing his rider at the start.