Lloyd Dobler had a boombox. John Cusack, in 2026, has something better: a full Say Anything screening and a seat onstage to answer every question you have ever wanted to ask him. On Friday, September 18, Cusack brings his touring Q&A series to Paramount Hudson Valley in Peekskill — one of the Hudson Valley's great old rooms — for a night that is equal parts cinema and conversation.
About the Evening
Say Anything came out in 1989 and has never really left. Cameron Crowe's feature directorial debut turned Cusack's Lloyd Dobler — an underachiever with big dreams and absolutely no plan — into one of the defining characters of a generation. Diane Court, played by Ione Skye, is the counterpart: brilliant, poised, and about to leave for England on an academic scholarship. The boombox scene. The trench coat. If you know, you know — and now you get to ask the guy who made it all work.
The format is straightforward: the full film screens first, then Cusack comes out for a live audience Q&A. He has been doing versions of this evening at theaters up and down the East Coast in 2026, and from all accounts it is a genuine open conversation — not a scripted talk, but a real back-and-forth about the film, the character, and what Lloyd Dobler has meant across thirty-plus years.
About John Cusack
Cusack broke through with a run of 1980s films — Say Anything, Sixteen Candles, The Sure Thing — before building one of the more interesting filmographies of the following decades. Grosse Pointe Blank, Being John Malkovich (which earned him an Independent Spirit Award nomination), and High Fidelity (a Golden Globe nomination in 2001) are the highlights of that stretch. He received a Hollywood Walk of Fame star in April 2012 and more recently appeared in the Prime Video series Utopia. The career rewards a rewatch — which is, conveniently, exactly what you are about to do.
Paramount Hudson Valley
The Paramount opened in 1930 and has been a fixture of downtown Peekskill ever since. The theater holds just over 1,000 seats across orchestra level and an elevated balcony, and it is the kind of room where the sightlines are genuinely good — which matters when part of the show is watching Cusack's face as he fields questions from the crowd. The venue runs cashless for concessions and merchandise, so leave the bills at home.
Peekskill sits about 50 miles north of Manhattan in Westchester County, and this Hudson Valley stop will pull an audience from both directions. Parking is available along Main Street; plan to arrive early, as the venue asks attendees to allow time for a security screening before doors open. Give yourself that buffer and you will be fine.
Tickets
Tickets are on sale now through the Paramount Hudson Valley box office. VIP packages — which include a premium seat and a meet-and-greet photo opportunity with Cusack — are also available. This tour has been selling steadily at every stop. Do not put it off.