From his breakout appearance as beloved stoner Jeff Spicoli in Fast Times at Ridgemont High to his Academy Award-winning efforts as a dramatic actor, Sean Penn has had a remarkable journey. This weekend, he’s adding “action hero” to his résumé with The Gunman, so in honor of Mr. Penn’s cinematic exploits, we decided to dedicate this week’s list to some of the brightest highlights from his distinguished (and quite eclectic) filmography. It’s time for Total Recall!
Before New Jack City and the decade of hard-hitting urban cop dramas that followed, there was 1988’s Colors, starring Penn and Robert Duvall as a pair of LAPD officers out to purge the streets of gang activity — when they aren’t clashing with one another over their conflicting methods of serving and protecting the public, that is. There’s truly no shortage of movies that start from the same rough setup, but director Dennis Hopper — working from a script by Crimson Tide writer Michael Schiffer — had a tremendous cast to work with, including a roster of solid supporting players (among them Maria Conchita Alonso and Don Cheadle) to ground what might otherwise have proven an overly familiar tale. “There’s great pleasure in watching these two actors work,” wrote Hal Hinson for the Washington Post. “And Hopper, a great actor himself, knows what they need to thrive.”
Director Phil Joanou opened his career with a better-than-average teen comedy (Three O’Clock High) and a well-intentioned, albeit indulgent rockumentary (U2: Rattle and Hum) — which is to say that few could have expected that he had it in him to helm a drama as tense and gripping as 1990’s State of Grace. Starring Penn as an undercover cop whose latest case tests his loyalty to his best friend (played by Gary Oldman) — not to mention his affection for his friend’s sister (Robin Wright) — Grace exploited an instantly recognizable formula while transcending it thanks to outstanding acting from its leads. Calling it “a superior gangland drama that deals imaginatively with the familiar themes of family, friendship and loyalty,” Don Groves of SBS wrote, “Wild-eyed and sporting lank, greasy hair, Oldman dominates the screen as a truly terrifying character, while Penn effectively portrays a man battling with diametrically-opposed emotions.”
By the time Casualties of War arrived in 1989, filmgoers had already seen a growing list of films about the wretched aftermath of the Vietnam War, including dramatic hits such as The Deer Hunter, Apocalypse Now, and Platoon as well as action-driven blockbusters like the Rambo trilogy — which might go a little way towards explaining why they failed to show up for Brian De Palma’s Casualties of War, in which Penn and Michael J. Fox take opposing sides in the nightmarish conflict within an American patrol squad that erupts as the war rages on around the soldiers. A solid hit with critics who offered Penn another round of hosannas and expressed surprised admiration for Fox’s strong dramatic turn, Casualties lost money at the box office while earning praise from scribes such as Michael Wilmington of the Los Angeles Times, who wrote, “There’s a moral charge to the action, but it’s also swooningly exciting, coldly scary. Every friend may be an enemy, every innocent a traitor.”
The ’80s produced no shortage of Cold War dramas, but 1985’s The Falcon and the Snowman is utterly unlike any of them. Rather than a pulse-pounding thriller coasting on patriotism-driven intrigue, this fact-based, John Schlesinger-directed effort stars Penn as an opportunist drug dealer who finds himself lured into selling government secrets after he’s approached by a defense contractor (Timothy Hutton) who becomes disillusioned after realizing the U.S. government’s overseas activities aren’t always as noble as he’d once believed — and whose rather impulsive decision to commit treason soon finds both men struggling to control forces well beyond their control. “It’s a watchable, likely accurate recitation of facts, with two outstanding performances,” wrote Nick Rogers for Suite101. “But in the case of The Falcon and the Snowman, the truth we don’t see onscreen may be stranger, and stronger, than the historical fiction that has been created.”
Nothing gets a cineaste’s anticipation humming like news of a new Terrence Malick film — and since Malick is nothing if not deliberate, we had plenty of time to hum over Tree of Life. Originally announced in the wake of Malick’s 2005 effort The New World, it tumbled down the release schedule throughout 2009 and 2010 before finally bowing in May 2011 — all 139 inscrutable minutes of it. The product of Malick’s progressively harder-to-contain ambition, Life took viewers from the dawn of life to the 21st century, leaving plenty of room for solid acting from Penn, Brad Pitt and Jessica Chastain — as well as hosannas from critics like the Wall Street Journal’s Joe Morgenstern, who deemed it “Daring in concept, occasionally daffy in execution and ultimately unforgettable” as well as “a heartfelt answer to the question of where we humans belong — with each other, on this planet, bound by love.”
1986 was the best of times and the worst of times for Sean Penn in the critics’ circle: August brought the roundly derided Shanghai Surprise, co-starring our subject and his newlywed bride Madonna in one of the decade’s most infamous flops, but April found him in a different — and altogether more successful — kind of family affair. At Close Range placed Penn alongside his brother Chris in director James Foley’s bleak crime drama about a mob boss (a mustachioed Christopher Walken) whose return from exile upends the lives of his grown sons. In spite of its compelling story and excellent cast — which included Mary Stuart Masterson, Kiefer Sutherland, and Crispin Glover — the movie didn’t make much of an impact at the box office, but it resonated with critics like James Sanford of the Kalamazoo Gazette, who called it “a dark jewel of a drama, with first-rate performances.”
Hollywood stories about childhood loyalties divided by adult lives that unfold on opposite sides of the law aren’t exactly in short supply, and really never have been — but when you have Clint Eastwood behind the camera, Brian Helgeland writing the script from a Dennis Lehane book, and a cast packed with reliable names like Penn, Laura Linney, Marcia Gay Harden, Tim Robbins, Kevin Bacon, and Laurence Fishburne, you’re pretty much guaranteed a terrific movie. That’s exactly what filmgoers got with 2003’s Mystic River, which transcended its rather familiar framework to earn over $150 million at the box office and a pair of Oscars, including one awarded to Penn for his portrayal of Jimmy Markum, a gangster whose life is upended when his daughter is murdered — and the investigation rekindles his connection with an old friend (Bacon) who’s grown up to be a police detective and has to face the possibility that the crime was committed by another of their youthful buddies (Tim Robbins). It sounds like the stuff of bullet-riddled melodrama, but few mainstream authors spin literary gold out of pulp as reliably as Lehane, and with Eastwood’s flinty direction providing a solid foundation for his stellar cast, River deserved the praise of critics such as Eleanor Ringel Gillespie of the Atlanta Journal-Constiution, who wrote, “Eastwood has handed Penn the role of a lifetime, and the actor scorches the screen with his anguish and angry vengefulness.”
The word “iconic” is sorely overused, but Penn’s portrayal of the blissfully zonked stoner Spicoli in Fast Times at Ridgemont High richly deserves it — and it was followed by a complete 180 in 1983’s Bad Boys, a grim teen drama from director Rick Rosenthal about a petty hood (Penn) whose thirst for bigger scores puts him on a collision course with a rival (Esai Morales) that ultimately lands them both in the same hellish juvenile correctional facility. While plenty of critics took issue with Bad Boys‘ unrelentingly dark tone (and expressed astonishment that it was directed by the same person responsible for Halloween II), most agreed that whatever the movie’s problems, it was substantially elevated by powerful performances from its stable of young actors, most particularly Penn. “Bad Boys misses its chance at greatness, but it’s saying something that this movie had a chance,” mused Roger Ebert. “I have a notion it will stand as one of those benchmark movies that we’ll look back at for the talent it introduced.”
Nine times out of 10, when you see a movie poster that focuses on a man and a woman, their characters are romantically involved. Not so 1995’s true events-inspired Dead Man Walking, starring Penn as a death row inmate and Susan Sarandon as Sister Helen Prejean, the real-life nun whose experiences advocating on behalf of a pair of convicted killers inspired her to write the non-fiction book of the same name — and pursue a life of speaking out against the death penalty. It’s harrowing stuff all the way around, ably adapted by writer-director Tim Robbins and achingly brought to life by his cast; both Penn and Sarandon as well as Robbins were nominated for Oscars in their respective categories, and while Sarandon was the only one who won, each of the trio were lauded by critics for their part in what the Washington Post’s Hal Hinson deemed “An intelligent, balanced, devastating movie.”
Actors have earned acclaim for starring roles in biopics often enough that it’s easy to be cynical about the genre as a whole — but it’s just as easy to understand why Penn picked up his second Best Actor Oscar for his work in Milk. Directed by Gus Van Sant from a Dustin Lance Black screenplay, it stars Penn as Harvey Milk, the activist whose promising political career was cut short when he was assassinated by a fellow member of the San Francisco Board of Supervisors in 1978, and surrounds his wholly committed performance with stellar contributions from a talented stable that also included James Franco, Emile Hirsch, and Josh Brolin as Milk’s killer Dan White. While it wasn’t a massive box office hit, Milk more than made up in plaudits what it lacked in dollar grosses, with more than a few critics singling out Penn for praise in a production with no shortage of brilliance. As Andrew O’Hehir wrote for Salon, “I don’t know that this is Penn’s best performance, overall — let’s have that debate some other time — but as far as the mannered, immersive impersonations of his later career go, Harvey Milk takes the cake.”
Finally, here’s a compilation of some of Penn’s best moments as the legendary Spicoli in Fast Times at Ridgemont High:
