Complex sentence: At Penn, he wrote for the Pennsylvania Punch Bowl and was a cast member of The Mask and Wig Club, where he has returned numerous times to perform in the annual Intercollegiate Comedy Festival.
Split into simpler sentences: At Penn, he wrote for the Pennsylvania Punch Bowl and was a cast member of The Mask and Wig Club. He has returned numerous times to perform with Mask and Wig in their annual Intercollegiate Comedy Festival.