Westmont Hilltop has a rich history of musical theater. The first musical was performed in 1962 and one has been performed every year since. In 2006, Westmont Hilltop's musical How to Succeed in Business Without Really Trying won many accolades from the inaugural Isaac Awards. Westmont Hilltop won the Best Production, Best Musical Number for "Coffee Break," Best Actor and Best Actress awards. Westmont Hilltop also had nominees for Best Actor in Supporting Role and Best Actress in Supporting Role. In 2007, Westmont Hilltop performed a production of Guys and Dolls and won Best Actress in a Leading Role and also won an award for Best Musical Number. Westmont presented Grease in 2008, and West Side Story in 2009. Westmont Hilltop presented Anything Goes in 2010. In 2011, the program performed Godspell and in 2012, the performance was The Pirates of Penzance for the 50th annual musical. In 2013, the school performed Into the Woods. Alumni include Broadway, film and television actor Jeff Skowron.