Some of Kelley's most famous photo subjects have included Gary Cooper, Greta Garbo, James Cagney, Clark Gable, Winston Churchill, Bob Hope, Marlene Dietrich, Joan Crawford, Jack Benny, David Bowie, John F. Kennedy, Dwight D. Eisenhower, Franklin D. Roosevelt, Yma Sumac and, of course, Marilyn Monroe, with and without clothes.

Kelley was one of the judges for the famed annual Cavalcades of Jazz beauty contests from 1955 to 1958 which was held at Wrigley Field in Los Angeles and the last one at The Shrine Auditorium.

[2] These concerts and beauty pageants were produced by an African-American Leon Hefflin, Sr.[3] Kelley appeared in the 1966 documentary film The Legend of Marilyn Monroe.

Featuring Kelley's now-classic photo of Marilyn Monroe on the cover of its very first issue significantly factored in Playboy's launch into popularity, selling over 50,000 copies.

Continuing to partner with Hefner for future editions, Kelley always seemed to make his models more relaxed in order to obtain uniquely appealing and popular photos.

One model, Neva Gilbert, Miss July 1954, remembered the experience in a 2016 Associated Press interview, again recalling how he would always bring his wife with him to the shoots.

Tom Kelley Jr. attempted to auction off not only his father's photographs of Marilyn Monroe, but also their intellectual property rights such that the buyer could remarket them in any way they so chose.