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“The fact that these fine gents are sitting together shows the respect they have for each other,” said One Battle After Another director Paul Thomas Anderson (PTA) as he presented his three stars — Academy Award nominated actors Leonardo DiCaprio, Sean Penn, and Benicio Del Toro — with SBIFF’s 2026 Hammond Cinema Vanguard Award last night.
“I’ve waited my whole life to work with these guys,” said DiCaprio earlier in the evening at the Arlington, in a moderated discussion with renowned film critic Pete Hammond, who, together with his wife Madelyn Hammond, has the award named in his honor.
Leonardo DiCaprio at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Benicio del Toro greets fans at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Excited fans at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Sean Penn and Benicio del Toro at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Sean Penn and Benicio del Toro at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Sean Penn and Benicio del Toro at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Photographers snapping shots of Sean Penn and Benicio del Toro at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Benicio de Toro outside at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom
Between clips that barely were able to touch the surface of their long careers, the actors discussed the past and current trajectories of their work and coming together for their critically acclaimed comedy-action-thriller One Battle After Another, which was 20 years in the making, and has received 13 nominations at the 98th Academy Awards.
In addition to discussing their experiences on that film, the conversation also touched on DiCaprio’s work What’s Eating Gilbert Grape, The Revenant, and The Wolf of Wall Street. Del Toro recounted his experiences working on Traffic, The Pledge, and 21 Grams, in which he also worked with Sean Penn. And Penn discussed work in Hurlyburly and All the King’s Men.
They also touched on their roles in The Phoenician Scheme (Del Toro), Once Upon a Time in Hollywood (DiCaprio), and Milk (Penn).
“Getting wonderful writing is, it turns out, still the best gift that we can get for a movie,” said Penn.
SBIFF Executive Director Roger Durling at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Honorees greeting host Pete Hammond at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Leonardo DiCaprio at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Leonardo DiCaprio, Sean Penn, and Benicio del Toro at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Leonardo DiCaprio, Sean Penn, and Benicio del Toro at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Leonardo DiCaprio, Sean Penn, and Benicio del Toro at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Leonardo DiCaprio, Sean Penn, and Benicio del Toro at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Leonardo DiCaprio at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Leonardo DiCaprio greets Director Paul Thomas Anderson at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Paul Thomas Anderson, Leonardo DiCaprio, Sean Penn, and Benicio del Toro at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Sean Penn, Benicio del Toro, and Leonardo DiCaprio with their trophies at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
Sean Penn, Benicio del Toro, and Leonardo DiCaprio with their trophies at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom 
From left, Pete Hammond, Sean Penn, Benicio del Toro, Leonardo DiCaprio, and Paul Thomas Anderson at the SBIFF Hammond Cinema Vanguard Awards, Arlington Theatre, February 9, 2926 | Photo: Ingrid Bostrom
All three actors expressed their admiration for PTA’s skills as both a writer and director. This was their last appearance on behalf of promoting One Battle After Another before the Oscar’s, and they definitely made the most of it.
“To me, this is on the level of having Brando, Pacino, and Cann all together in The Godfather,” said Hammond of the talented actor trifecta.
For more on the evening with Leonardo DiCaprio, Sean Penn, and Benicio Del Toro, see Josef Woodard’s story.
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