In 1944, after a string of leading ladies that included some of the most beautiful young actresses in Hollywood, Dale Evans joined Roy in The Cowboy and the Senorita. Together, they starred in 28 films. Roy and Trigger, along with Dale Evans, Gabby Hayes, and the Sons of the Pioneers, formed one of the greatest movie teams of all time Dale was no slouch herself:

As Dale Evans, she ultimately reached Chicago, home of great music and talented bands. She became a vocalist with a number of different "big bands" and was featured soloist in such notable hotels as the Blackstone (Balinese Room), the Sherman (Panther Room, along with jazz legend, Fats Waller), the Drake (Camellia Room) and the Chez Paree Supper Club. Anson Weeks hired her as vocalist for his orchestra just as they began a major tour to the West Coast. After a two-month stand at The Coconut Grove, Dale left the Orchestra and returned to Chicago where she was hired as staff singer for radio station WBBM, the local CBS affiliate. Talent scouts from Paramount Studios discovered her and arranged a screen. test in Hollywood for the movie, Holiday Inn, starring Fred Astaire and Bing Crosby. Dale's dancing wasn't quite up to Astaires', so she didn't get the part. Her agent, however, showed her screen test to 20th Century Fox studios where she received a one-year contract. This resulted in only small parts in two pictures, Orchestra Wives and Girl Trouble. Dale then signed with the top ranked Chase and Sanborn Show which was broadcast nationwide. Featured as regulars with Dale were Don Ameche, Jimmy Durante, Edgar Bergen (Candice Bergen's father) and Charlie McCarthy. Weekly guests read like a Who's Who of the entertainment industry.

This exposure caused Republic Studios to sign her to a one-picture contract (Swing Your Partner) with a one-year option. The option was exercised and she was cast in several contemporary movies and one John Wayne western in which her singing was featured.

Herbert Yates, head of Republic Studios was inspired by the successful stage play, Oklahoma, and decided to expand the female lead in westerns and adopt this format for one of his biggest stars, Roy Rogers. Dale, he reasoned, had a large following and reputation as a singer and, being from Texas, could surely ride 'n rope. His reasoning proved correct on the former but somewhat suspect on the latter. Nevertheless, history was made and destiny seemingly fulfilled in 1944 with release of The Cowboy and The Senorita - the first of 28 films they would make together. This on-screen team became an off-screen team on New Year's Eve, 1947. They were married on the Flying L Ranch in Davis, Oklahoma, where they had just completed filming Home in Oklahoma. The owner of the ranch, when he learned they were to be married, offered the ranch as a wedding site.

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