This Is the Army (1943)
A future U.S. senator (George Murphy) and a future president (Ronald Reagan) starred in this wartime flick. Written by Irving Berlin, the film resurrects the WWI show he wrote as soldier in 1918 and includes a rousing Kate Smith performance of "God Bless America."
Holiday Inn (1942)
If you like Berlin's music, you'll enjoy this 1942 musical that features a dozen of his songs. An all-star cast including Bing Crosby, Fred Astaire, Virginia Dale, and Marjorie Reynolds anchored this blockbuster hit. The film also contains a now-controversial minstrel scene in which Crosby performs in blackface.