Cleale made his Broadway debut in the 1995 Johnny Burke revue "Swinging on a Star", for which he received a Drama Desk Award nomination as Outstanding Featured Actor in a Musical. Additional Broadway credits include the 1996 revival of "Once Upon a Mattress" with Sarah Jessica Parker, the ill-fated 2002 Michel Legrand musical "Amour", and the 2005 hit "Spamalot". Cleale also appeared in the popular revue "I Love New York" which was done at the Rainbows and Stars room along with Bryan Batt, Janet Metz and Heather MacRae. Off-Broadway, he has appeared in "Call Me Madam" opposite Tyne Daly and "A New Brain" with Malcolm Gets and Kristin Chenoweth for Lincoln Center Theater.