5 Best Movies to Watch by Sean Penn

Staff & contributors

Poignant, delightful, and simply gorgeous, Licorice Pizza just might be Paul Thomas Anderson's best work to date. The period dramedy follows two young people, one in her 20s and one in his teens, as they strike an unlikely but lovely friendship and try to find their place in the world. They may be 10 years apart, but they're stuck in the same swirl of rejection and confusion that trap a lot of ambitious people like them. The premise is far from original, but Alana Haim and Cooper Hoffman turn in captivating performances (made even more impressive by the fact that this is both their film debut). There is an ease and naturalism to both their chemistry and onscreen performances that’s hard not to love.

The thick and wistful patina of the ‘70s, the comedic asides, and the colorful supporting cast all also help paint an overall charming picture that shouldn't be missed.

Genre: Comedy, Drama, Romance

Actor: Adam Somner, AJ Carr, Alana Haim, Alex Canter, Alex Herschlag, Allegra Clark, Anna Cordell, Anthony Molinari, Ariel Rechtshaid, Benjamin Barrett, Benny Safdie, Bottara Angele, Bradley Cooper, Cassandra Kulukundis, Charlotte Townsend, Christine Ebersole, Ciara Williamson, Cooper Hoffman, Craig Stark, Dan Anderson, Danielle Haim, Danielle Miller, Delaina Mitchell, Demelza Cronin, Destry Allyn Spielberg, Dick Rudolph, Eloy Perez, Emily Althaus, Emma Dumont, Erica Sullivan, Este Haim, Fatimah Hassan, George DiCaprio, Gerren Hall, Harriet Sansom Harris, Hazel Schaffer, Ingrid Sophie Schram, Isabelle Kusman, Iyana Halley, Jeff Willy, John C. Reilly, John Michael Higgins, Jon Beavers, Jonathan Goetzman, Joseph Cross, Karen Kilgariff, Kat Barnette, Kimiko Kasai, Kirk Saduski, Lakin Valdez, Laura Gary, Laura Louise Richardson, Liz Cackowski, Louis Delavenne, Mark Flanagan, Mark Wolfson, Mary Eileen O'Donnell, Mary Elizabeth Ellis, Max Mitchell, Maya Rudolph, Mick Giacchino, Nate Mann, Paige Locke, Patrick Salway, Pearl Minnie Anderson, Ray Chase, Ray Nicholson, Richard B. Larimore, Rogelio Camarillo, Ryan Heffington, Sasha Spielberg, Savannah Ioakimedes, Sean Penn, Skyler Gisondo, Steven Herrera, Tim Conway Jr., Tom Waits, Tyler Young, Waylon Richling, Yumi Mizui, Zoe McLane

Director: Paul Thomas Anderson

Told with grace and maturity without sensationalizing its subject matter, Dead Man Walking expertly walks the line between taking a moral stand and keeping the messy humanity of its characters intact. Though it may seem just like a legal drama or prison film on the surface, writer/director Tim Robbins weaves in commentary on class and the role religion is expected to play in middle class Southern communities—especially in the context of justice and crime. Sean Penn and Susan Sarandon (in the role that won her her Oscar) play every side to this drama with remarkable control, building an unlikely rapport that culminates in a finale that's as moving as any great tear-jerker. It may be tough to watch at times, given the raw emotions that are laid bare, but Dead Man Walking remains relevant even today.

Genre: Drama

Actor: Adam Nelson, Adele Robbins, Anthony Michael Frederick, Arthur Bridgers, Barton Heyman, Celia Weston, Clancy Brown, Codie Scott, Cortez Nance Jr., Dennis Neal, Eva Amurri Martino, Helen Prejean, Jack Black, Jack Henry Robbins, Jenny Krochmal, Jeremy Knaster, Joan Glover, Jon Abrahams, Kevin Cooney, Larry Pine, Lenore Banks, Lois Smith, Marcus Lyle Brown, Margo Martindale, Michael Cullen, Miles Robbins, Missy Yager, Molly Bryant, Nesbitt Blaisdell, Pamela Garmon, Pete Burris, Peter Sarsgaard, R. Lee Ermey, Ray Aranha, Raymond J. Barry, Robert Prosky, Roberta Maxwell, Scott Sowers, Scott Wilson, Sean Penn, Steve Boles, Steve Carlisle, Susan Sarandon, Thomas McGowan

Director: Tim Robbins

This emotionally rich biopic spans Reinaldo Arena’s lifetime, from his childhood and early embrace of the Cuban Revolution to his deportation via the notorious 1980 Mariel boatlift, and subsequent death in the United States. The story of Arenas’ life is told through using his own words, over director Julian Schabel's beautifully crafted images. In his first-ever English-speaking role, Javier Bardem renders a strong dramatic performance for which he deservedly received wide acclaim. Before Night Falls is a finely crafted portrait of a creative yet self-destructive poet who has to face the clash between his identity and the political environment surrounding him.

Genre: Drama

Actor: Abel Woolrich, Alfredo Villa, Andrea Di Stefano, Antonio Zavala Kugler, Batan Silva, Carmen Beato, Claudette Maillé, Diahnne Abbott, Diahnne Déa, Diego Luna, Eduardo Arroyuelo, Ewa Piaskowska, Filiberto Estrella, Francisco Gattorno, Giovani Florido, Héctor Babenco, Javier Bardem, Jerzy Skolimowski, John Ortiz, Johnny Depp, Jorge Zárate, Jorge Zepeda, Julian Bucio, Khotan Fernández, Lia Chapman, Lola Schnabel, Loló Navarro, Manolo García, Mario Oliver, Marisol Padilla Sánchez, Matthias Ehrenberg, Maurice Compte, Michael Wincott, Najwa Nimri, Ofelia Medina, Olatz Lopez Garmendia, Olivier Martinez, Patricia Reyes Spíndola, Pedro Armendáriz Jr., René Pereyra, Rene Rivera, Santiago Magill, Sean Penn, Stella Schnabel, Vincent Laresca, Vito Schnabel, Zulema Cruz

Director: Julian Schnabel

, 2024

If you’re coming into this expecting to relive your favorite ‘80s coming-of-age moments from The Breakfast Club to St. Elmo’s Fire, then you’ll get a taste of that, but don’t expect to be fully satisfied. Instead, the reunion that happens in Brats resembles group therapy more than anything. Here, director Andrew McCarthy (Pretty in Pink, St. Elmo’s Fire) seems to be on a journey to heal from his troubled past, which he believes was caused, in part, by a defamatory article that called him and a crop of young actors in the ‘80s “The Brat Pack.” The film follows McCarthy as he travels across the country to discuss the label with fellow Brat Packers, who funnily enough, don’t share his contempt for it. Sure, they’re annoyed, but they’ve moved on for the most part. McCarthy on the other hand doesn’t possess the self-awareness to know this, which is perhaps why he’s fallen trap to the Streisand Effect. “The Brat Pack” isn’t nearly as negative as he thinks it to be, but because he keeps ranting about it, I’m starting to think the accusations might be true--he just might be the vain and entitled celebrity, the brat, he claims he’s not. That said, the documentary has its moments. The way it’s modestly filmed is charming and inventive, the artful blend of old footage and 80s music hits the nostalgic spot, and the conversations can be interesting. Who would’ve thought Demi Moore would be the wisest person in the room?

Genre: Documentary

Actor: Ally Sheedy, Andrew McCarthy, Bret Easton Ellis, Demi Moore, Emilio Estevez, Eric Stoltz, Howard Deutch, Jacqueline Bisset, James Spader, Joel Schumacher, John Ashton, John Cusack, John Hughes, Jon Cryer, Judd Nelson, Lea Thompson, Marci Liroff, Molly Ringwald, Phil Donahue, Richard Schickel, Rob Lowe, Sammy Davis Jr., Sean Penn, Timothy Hutton, Tom Cruise

Director: Andrew McCarthy