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Wellesley High’s upcoming production of ‘Legally Blonde: The Musical’ promotes confidence through entertainment

Story Center by Story Center
December 3, 2025
Reading Time: 7 mins read
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Legally Blonde: The Musical, Wellesley High

All photos by Declan Kashou

Wellesley High School students on Dec. 4-6 will present “Legally Blonde: The Musical,” a high-energy show that promises lots of laughs.  The musical is inspired by the 2001 hit film, which tells the story of Elle Woods, a bubbly student navigating law school at Harvard.

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In the musical, Elle (played by Samantha Hirschey) eagerly hopes her boyfriend, Warner Huntington III (played by Oliver Zinggeler), will propose to her. When he decides she is too “blonde” for him and seeks someone more serious, Elle uses her intelligence and charm to prove that her personality is an asset, not a liability. Along the way, she meets several memorable characters: Paulette (Anay Ayala), a shy but lovable manicurist; Emmett Richmond (Jack White), a charming teaching assistant; and Vivienne Kensington (Callie Pillsbury), Warner’s polished new girlfriend.

This is the second Wellesley High School musical directed by Mr. Skylar Grossman, whose philosophy focuses on alternating between contemporary and classics. He believes the show is unique for students to perform because it uses an entertaining medium to confront misogyny and promote self-discovery. He also emphasizes the importance of teamwork, encouraging students to support and learn from each other during rehearsals. Ultimately, he wants the production to teach students about different styles of musical theater.

Legally Blonde is known for its upbeat and poppy soundtrack, featuring plenty of belting and exciting dance numbers. One standout, “Whipped into Shape,” is based on Brooke Wyndham’s (Lucy Gandler) workout tape. This sequence takes place in a prison, with the ensemble jumproping while singing. “While physically demanding, it will be incredibly exciting for the audience to watch!” students in the number say.

The musical also includes slow numbers, like “Serious,” sung by Warner and Elle, who humorously walk the audience through their dinner breakup. Musical director Brandon Santini works closely with the cast to convey the depth of these moments through guided practice and encouraging students to engage with the music independently. These songs provide contrast to the show’s high-energy numbers, allowing the audience to connect more deeply with the characters’ journeys.

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Tech week for Legally Blonde runs from Nov. 24 through Dec. 3. During this time, the cast and crew have been spending up to eight hours a day refining choreography, music, and stagecraft. All the challenges of producing a show of this caliber culminate in four final performances. The production’s ultimate goal is to inspire audiences with its message: setbacks can be turned into advantages, and hard work and determination can lead to success. It also serves to showcase the talent and dedication of Wellesley High’s Drama Society.

Tickets can be purchased online or at the door via cash or check if any remain. 

Performances:

  • Thursday, Dec. 4 at 7pm
  • Friday, Dec. 5 at 7pm
  • Saturday, Dec. 6 at 2pm & 7pm

Legally Blonde: The Musical, Wellesley High

Legally Blonde: The Musical, Wellesley High

Legally Blonde: The Musical, Wellesley High


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‘ The preceding article may include information circulated by third parties ’

‘ Some details of this article were extracted from the following source theswellesleyreport.com ’

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