In 1959, Van Dyke landed a small part in the Broadway comedy review Girls Against the Boys. The show only lasted two weeks, and he soon moved on to another production. Along with Chita Rivera, Paul Lynde and Charles Nelson Reilly, Van Dyke was cast in the musical Bye Bye Birdie, which made its Broadway debut in 1960. The musical proved to a big hit, and it brought Van Dyke his one and only Tony Award win in 1961, for his supporting role. Not long after, his career took off.
Van Gogh had a catastrophic love life. He was attracted to women in trouble, thinking he could help them. When he fell in love with his recently widowed cousin, Kate, she was repulsed and fled to her home in Amsterdam. Van Gogh then moved to The Hague and fell in love with Clasina Maria Hoornik, an alcoholic prostitute. She became his companion, mistress and model.
In November 1959, Van Dyke made his Broadway debut in The Girls Against the Boys. He then played the lead role of Albert Peterson in Bye Bye Birdie, which ran from April 14, 1960, to October 7, 1961. In a May 2011 interview with Rachael Ray, Van Dyke said that when he auditioned for a smaller part in the show he had no experience as a dancer, and that after he sang his audition song he did an impromptu soft-shoe out of sheer nervousness. Gower Champion, the show's director and choreographer, was watching, and promptly went up on stage to inform Van Dyke he had the lead. An astonished Van Dyke protested that he could not dance, to which Champion replied: "We'll teach you". That musical won four Tony awards including Van Dyke's Best Featured Actor Tony, in 1961. In 1980, Van Dyke appeared as the title role in the first Broadway revival of The Music Man.