Gary Crosby, Carol Lynley, Clifton Webb, and Jane Wyman in Holiday for Lovers (1959)

Sal Mineo, Barry Coe, and Gary Crosby in A Private's Affair (1959)

Sal Mineo, Barbara Eden, Barry Coe, and Gary Crosby in A Private's Affair (1959)

Gary Crosby and Bonnie Beecher in The Twilight Zone (1959)

Dennis Crosby, Gary Crosby, and Phillip Crosby

Mel Brooks, Jerry Lewis, and Gary Crosby in The Ladies Man (1961)

Frank Sinatra and Gary Crosby 1954 Photo by Gabi Rona

Ciro's Nightclub Gary Crosby & Sammy Davis Jr.

Sal Mineo, Barbara Eden, Christine Carère, Barry Coe, Gary Crosby, and Terry Moore in A Private's Affair (1959)

Gary Crosby and Carol Lynley in Holiday for Lovers (1959)

Barbara Eden and Gary Crosby in A Private's Affair (1959)

Sal Mineo, Jim Backus, Barbara Eden, and Gary Crosby in A Private's Affair (1959)

Sal Mineo, Barbara Eden, and Gary Crosby in A Private's Affair (1959)

Sal Mineo, Barbara Eden, Barry Coe, Paul Comi, Gary Crosby, and Hideo Inamura in A Private's Affair (1959)