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Caleb Hearon is living his dream. The 31-year-old comedian gushed about working with Anne Hathaway at the Devil Wears Prada 2 premiere on April 20. For Hearon, landing this role closes a nostalgic circle from his childhood.
🔥 Quick Facts
- Premiere Date: April 20, 2026 in New York City marks the world premiere event for the sequel
- Caleb’s Age: The comedian and podcast host is 31 years old, playing Miranda’s new second assistant
- Iconic Connection: Hearon watched the original film at 11 years old as a closeted gay kid in Missouri
- Release Date: The Devil Wears Prada 2 arrives in theaters on May 1, 2026 for all audiences
Caleb’s Gushing Praise for Anne Hathaway on Set
Hearon couldn’t contain his enthusiasm when describing his experience with Hathaway, 43. Speaking to People at the New York City premiere, he called the interaction “fabulous.” The comedian emphasized how nice and genuine Hathaway was throughout filming. Hearon revealed that they didn’t discuss acting techniques or professional advice between scenes.
Instead, Hearon and Hathaway bonded over personal conversations and simply enjoyed time together. “It was lovely,” he reflected, describing their chemistry as natural and comfortable. The experience exceeded Hearon’s wildest expectations for collaborating with the Hollywood icon.
Caleb Hearon raves about Anne Hathaway at Devil Wears Prada 2 premiere
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From Childhood Fantasy to Professional Reality
Caleb Hearon watched The Devil Wears Prada original as an 11-year-old closeted gay kid in Missouri, finding solace and inspiration in the film’s iconic fashion world. The movie meant everything to him during a formative yet hidden period of his life. Years later, Hearon transformed from dedicated fan to professional actor stepping onto the same cinematic stage.
The casting represents a full-circle moment for the “So True” podcast host who built his career as a comedian and internet personality. Hearon plays Charlie, the current second assistant to Miranda Priestly, the role originally defined by Hathaway’s Andy Sachs two decades ago. His 11-year-old self would never have imagined this possibility.
The Ensemble Cast Brings Fashion Forward
| Role | Actor |
| Charlie (New Second Assistant) | Caleb Hearon |
| Andy Sachs (Returning) | Anne Hathaway |
| Miranda Priestly (Returning) | Meryl Streep |
| Nigel Kipling (Returning) | Stanley Tucci |
The Devil Wears Prada 2 brings back the original cast while introducing exciting new talent to the world of high fashion filmmaking. Hearon joins established names including Meryl Streep, Anne Hathaway, Emily Blunt, and Stanley Tucci in this highly anticipated sequel. The chemistry between returning veterans and fresh faces creates compelling new storylines for audiences.
Hearon’s casting proves the franchise values bringing diverse voices to iconic narratives. His journey from fan to cast member inspires young creators seeking their breakthrough moment in entertainment industry careers.
Stanley Tucci Steals the Diva Crown at Premiere
“I’m no question the cast diva. I’m awful, just terrible.”
— Stanley Tucci, Actor and Fashion Authority
Stanley Tucci brought his signature wit to premiere night, joking about his “diva” reputation on set. Anne Hathaway had previously teased during a Late Show appearance that Tucci was particular about his wardrobe choices. Tucci leaned into the characterization with charm, calling himself “no question” the production diva.
When a young interviewer suggested diva energy means confidence, Tucci eagerly agreed. His playful attitude showcased the camaraderie among cast members who clearly enjoyed their time together. Tucci’s return as Nigel Kipling brings the same fashion expertise and humor audiences loved from the original.
What Should Fans Expect When The Devil Wears Prada 2 Arrives?
The Devil Wears Prada 2 opens in theaters nationwide on May 1, 2026, just 10 days after the New York premiere. Director David Frankel returns to helm this fashion-focused sequel that explores where these characters stand 20 years later. Emily Blunt also reprises her iconic role as Emily Charlton, Andy’s former rival and friend.
This film marks the most anticipated release in the fashion comedy genre for 2026. Caleb Hearon’s presence adds fresh perspective while honoring the legacy of the beloved original. The convergence of seasoned talent and emerging voices promises to deliver both nostalgia and surprising new dimensions to the Runway magazine universe.
