In 1942, Benjamin enlisted in the US Army, and performed in and produced entertainment shows. After returning to civilian life, he joined with lyricist George David Weiss, and established a second successful songwriting partnership with him. The pair wrote some twenty hit songs over the next decade. Their early successes included "Oh! What It Seemed to Be", a 1946 hit for Frank Sinatra, Frankie Carle, and others; Perry Como's number 1 hit "Surrender"; and "Rumors Are Flying", a number 1 hit in 1946 for Frankie Carle and also a hit for the Andrews Sisters and others. They also wrote together for the Disney films "Fun and Fancy Free" and "Melody Time". Later hits written by Benjamin and Weiss included "I Don't See Me In Your Eyes Any More" (recorded by the Stardusters and Perry Como); "I'll Never Be Free" (a pop hit as a duet between Tennessee Ernie Ford and Kay Starr, and an R&B hit for both Dinah Washington and Louis Jordan); "Can Anyone Explain? (No, No, No!)" (The Ames Brothers); and "These Things I Offer You" (by Benjamin, Weiss, and Morty Levins, recorded by Sarah Vaughan). In 1952, Benjamin and Weiss wrote one of their most successful songs, "Wheel of Fortune", a number 1 hit for Kay Starr which sold over one million copies and provided the theme for a TV show.