Skyler Gisondo’s Booksmart Breakout: The Viral Self-Face Shirt Role That Defined a Cult Classic

The sight of Skyler Gisondo proudly sporting a T-shirt emblazoned with his own face in 2019’s Booksmart became an instant cinematic meme—a perfect metaphor for the film’s fearless, quirky charm. As Gisondo prepares to play Jimmy Olsen in James Gunn’s Superman, his scene-stealing turn as the endearingly awkward Jared reminds us why this underrated comedy remains essential viewing.

Why Booksmart Became an Instant Cult Classic

Directed by Olivia Wilde in her feature debut, Booksmart follows academic overachievers Amy (Kaitlyn Dever) and Molly (Beanie Feldstein) who discover their party-loving classmates also got into elite colleges. Their mission? Experience one epic night of high school revelry before graduation. United Artists Releasing’s sleeper hit masterfully blended raucous humor with genuine heart, earning a 97% Rotten Tomatoes score (May 2019). Critics like The New York Times’ Manohla Dargis praised its “fresh, feminist take on teen comedy.”

What elevates Booksmart beyond typical coming-of-age fare is its ensemble cast. Wilde assembled comedy veterans (Lisa Kudrow, Jason Sudeikis) alongside then-emerging talents: Billie Lourd’s unhinged Gigi, Diana Silvers’ cool-girl Hope, and Noah Galvin’s theatrical Alan. Each character subverts stereotypes—especially Gisondo’s Jared, whose wealth masks surprising depth. The film’s sharp script tackles Gen Z identity politics and queer awakening without cynicism, making its $25 million box office gross (Box Office Mojo) a baffling injustice to its brilliance.

Gisondo’s Jared: From Meme to Heartbeat

As Jared, Gisondo delivers a masterclass in comedic vulnerability. Introduced handing out custom T-shirts featuring his own face (“Last day of school present!”), Jared is a wealthy try-hard desperate for Molly’s approval. Gisondo layers the role with unexpected pathos—revealing Jared’s dreams of aerospace engineering and disdain for Broadway revivals. That self-printed shirt, now iconic, symbolizes Jared’s endearing need to be seen.

Gisondo’s performance showcased his range beyond child roles (The Santa Clause 3). His chemistry with Lourd’s chaotic Gigi—whether slow-dancing to Alanis Morissette or fleeing crime scenes—became the film’s comedic backbone. As Wilde told IndieWire (2019), “Skyler found Jared’s humanity beneath the absurdity. You laugh with him, never at him.” This role catapulted Gisondo into indie darling status, foreshadowing his casting as Superman’s iconic photographer.

Rediscovering Booksmart Today

Five years later, Booksmart’s themes of self-discovery and friendship resonate stronger than ever. It’s currently streaming on Max and available to rent on Prime Video/Apple TV. For Gisondo fans, it’s the perfect primer before his Superman debut—proving he can balance slapstick with soul.

Jared’s T-shirt remains a symbol of Booksmart’s fearless spirit—a comedy that celebrates weirdness while punching up at academic snobbery. As Gisondo joins the DC Universe, revisit the film that turned a meme into a milestone. Stream it tonight and witness the birth of a superhero sidekick in the making.

Must Know

Q: Where can I watch Booksmart in 2024?
A: Booksmart streams on Max and is available for digital rental/purchase via Prime Video, Apple TV, Vudu, and Google Play. Physical Blu-rays are also available.

Q: What other roles is Skyler Gisondo known for?
A: Beyond Booksmart, Gisondo starred in The Righteous Gemstones, Licorice Pizza, and Vacation. He’ll next appear as Jimmy Olsen in James Gunn’s Superman (2025).

Q: Did Booksmart win any major awards?
A: Yes! It won Best First Feature at the 2020 Independent Spirit Awards and earned Wilde a Directors Guild of America nomination for Outstanding Directorial Debut.

Q: Why is Booksmart considered groundbreaking?
A: The film redefined teen comedies with its female-led perspective, LGBTQ+ representation (Amy’s coming-out arc), and rejection of “smart vs. party” stereotypes. Wilde’s direction emphasized authentic teen voices.

Q: How did critics react to Skyler Gisondo’s performance?
A: Critics praised his balance of humor and heart. Variety noted he “steals scenes with delirious abandon,” while The Hollywood Reporter called Jared “a tragicomic masterpiece.”

Q: Will there be a Booksmart sequel?
A: No official plans exist, though Wilde expressed openness to reuniting the cast. Dever and Feldstein have both supported the idea.