From Thursday, May 14 to Saturday, May 16, 2026, student performers put on a vibrant performance of Wicked Sketchy, the annual sketch comedy performance held in King Theater. This year’s production—a program of 12 individual sketches by a cast of sixteen students—left members of the community hungry for more. The show has developed a reputation for finding humor in the things students and teachers love and care about, and this year was no different.
Benjamin Nass ’29, a Wicked Sketchy performer, described the daily workshopping process for the staff. The cast began by meeting to “propose for sketches and discuss what worked well with sketches and what wasn’t working.” Afterward, he described that students broke off “into small groups or individual [groups to] work on sketches of [their] choosing.” This process meant that every piece in Wicked Sketchy was student generated. Nass cited that the quick turnaround from writing to performing was a challenge: “we only really got the final versions of everything about two and a half weeks before opening night… people had to work very hard and most of these sketches had to be almost fully put together from the script at that time.”
This year’s show featured a mix of recurring favorites and brand-new material. Mark from Boston—a character featured for the third year in a row—returned this year in the sketch, Mark from Boston Runs for Mayor. Set to a parody of “Holding Out for a Hero,” the sketch demonstrated Mark’s campaigning for mayor in a full superhero costume. The crowd’s reaction to Mark’s return made it clear that recurring characters are audience hits. Additionally, one sketch that received significant attention was The Cell Phone Policy. The sketch poked fun at the school’s ongoing cell phone debate. Set to a parody of Lady Gaga’s “Telephone,” the sketch played out as a battle between students and teachers. Another crowd favorite was All That Math, a heartfelt and comedic tribute to Academic Dean and Upper School Math Teacher Heather Sugrue, who is leaving Milton at the end of the academic year. The cast performed a parody of “All That Jazz” from Chicago and drew much laughter and applause from the audience.
Kelli Edwards, the choreographer for all the dances in Wicked Sketchy, worked on three parodies. She began with a focus on lyrics and choreographed from there. Edwards shared that her job as a choreographer requires “making the lyrics and feelings in the song come to life.” For the Lady Gaga parody, she even went back and watched the original “Telephone” music video for inspiration.
The audience stepped away from the show impressed. Juliet Morse ’29 cited Wicked Sketchy as “one of [her] favorite productions this year.” She especially appreciated “how funny and entertaining it was. All of the different sketches were really fun to watch, and I enjoyed every single one of them.” Lila Feldman ’29 emphasized the hard work that she could tell had gone into the production. The play was “super memorable” and “well-thought out,” she said. Feldman added that “you could tell everyone put a lot of work and effort into it.” Isabella Vander Elst ’28 agreed, stating that she “enjoyed all the jokes in Wicked Sketchy [and] thought the acting was strong and the costumes, specifically The Cat in the Hat costumes, were super creative.” She also appreciated the set design.
Wicked Sketchy once again brightened the conclusion of the academic year for students. With sharp writing, creative choreography, and a dedicated cast, Wicked Sketchy brought students and staff together through laughs and memories. Looking back on the whole process, Nass stated that “overall [he] really enjoyed [his] time at the show and [believes] the fact that the school endorses this production really speaks to [its] values.”