Total Recall

Sean Penn's 10 Best Movies

In this week's Total Recall, we count down the best reviewed work of the Gunman star.

by | March 18, 2015 | Comments

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!


10. Colors (1988) 78%


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.”


9. State of Grace (1990)


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.”


8. Casualties of War (1989) 83%


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.”


7. The Falcon and the Snowman (1985) 82%


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.”


6. The Tree of Life (2011) 84%


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.”


5. At Close Range (1986) 87%


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.”


4. Mystic River (2003) 88%


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.”


3. Bad Boys (1983) 90%


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.”


2. Dead Man Walking (1995) 95%


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.”


1. Milk (2008) 93%


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:

Tag Cloud

USA Country Pet Sematary chucky japan Watching Series TCM trailers Disney Plus festivals TV renewals hispanic OWN Lionsgate spanish language Cosplay space ESPN Elton John streaming japanese Hallmark Ellie Kemper cinemax Box Office IMDb TV free movies TCA Winter 2020 popular Disney+ Disney Plus Holidays Vudu reboot TV debate television The Witch RT History scary Comic Book 2018 Apple sag awards Starz Ghostbusters Walt Disney Pictures Disney streaming service biography police drama Sundance TV Winners Spectrum Originals Binge Guide Calendar San Diego Comic-Con lord of the rings screen actors guild movie facebook films spain Hallmark Christmas movies 007 blockbuster PaleyFest classics based on movie Tubi Polls and Games Prime Video godzilla latino casting Trivia nbcuniversal docudrama thriller YouTube Premium AMC Plus Universal FX children's TV TIFF boxing screenings Rom-Com Columbia Pictures Grammys nfl Women's History Month CMT all-time Biopics Toys criterion SDCC toronto YouTube 24 frames slasher Film Festival CNN Stephen King DC streaming service cats 2016 true crime mob fresh monster movies Warner Bros. Action 2015 kaiju miniseries renewed TV shows NYCC HBO LGBT cartoon festival rt archives Crunchyroll HBO Max National Geographic docuseries 71st Emmy Awards PBS Academy Awards cooking Opinion Reality Competition period drama Mystery Countdown series basketball Reality Tags: Comedy dreamworks versus Pride Month news Film cancelled obituary black jamie lee curtis anthology art house The Walking Dead Superheroes scorecard suspense Pacific Islander Neflix Alien Turner Universal Pictures movies strong female leads Martial Arts Arrowverse Music zombie mcc anime Captain marvel Shudder supernatural king arthur Esquire 2021 TruTV 99% comics 93rd Oscars slashers Western doctor who Creative Arts Emmys Cartoon Network Comedy Emmys Mindy Kaling Classic Film Hollywood Foreign Press Association OneApp feel good Apple TV+ Anna Paquin cancelled TV shows tv talk zombies A24 Sony Pictures leaderboard cancelled TV series Netflix Christmas movies prank telelvision dark hollywood Song of Ice and Fire target Pirates History unscripted worst movies Food Network ID universal monsters 78th Annual Golden Globe Awards APB Nickelodeon Amazon Studios franchise Turner Classic Movies Animation BBC One crossover revenge BET Awards dogs Image Comics Apple TV Plus hidden camera The Academy Awards Tour Rocketman gangster sequels political drama disaster genre ABC richard e. Grant President women king kong black comedy Spike adventure Drama technology Discovery Channel GLAAD TLC witnail know your critic vs. Broadway justice league james bond Adult Swim RT21 Fargo Funimation 2020 Brie Larson venice Tomatazos Disney E! Election Chernobyl remakes First Look Superheroe SundanceTV a nightmare on elm street Fall TV emmy awards science fiction archives A&E FX on Hulu mutant 4/20 Freeform book adaptation halloween dexter Fantasy australia Disney Channel new zealand Amazon Prime ghosts documentaries sitcom Kids & Family new york critics First Reviews green book Holiday breaking bad stoner Black History Month aliens spy thriller Star Trek twilight rt labs video Nominations SXSW harry potter FOX canceled TV One The Walt Disney Company aapi Television Critics Association dragons spider-verse CBS cancelled television golden globe awards Tarantino Paramount Plus Thanksgiving 1990s rotten hist animated Quiz natural history Best and Worst vampires scary movies Dark Horse Comics football Sneak Peek kids Peacock Bravo adenture Epix superhero Fox News comic book movie psycho Premiere Dates NBC Valentine's Day scene in color Family VICE Mary Tyler Moore streaming movies Syfy BBC America Instagram Live 2019 ratings 90s Winter TV Sci-Fi DGA rotten movies we love Pixar The CW crime drama Mary Poppins Returns DirecTV Trailer elevated horror Rocky Super Bowl WGN VOD Baby Yoda BAFTA romance parents sequel 73rd Emmy Awards TV Land legend Photos Video Games historical drama YA book TCA 2017 theme song high school USA Network worst best Marvel Studios TV movies pirates of the caribbean canceled TV shows Musical Cannes wonder woman zero dark thirty See It Skip It Horror Character Guide Paramount razzies foreign Hear Us Out transformers olympics singing competition Rock heist movie Ovation 21st Century Fox new star wars movies ABC Family discovery comiccon El Rey American Society of Cinematographers international politics Legendary documentary DC Comics medical drama Mudbound Writers Guild of America ABC Signature CBS All Access directors sports Marathons Podcast dramedy Christmas Comics on TV Star Wars young adult Awards finale Chilling Adventures of Sabrina spinoff laika composers 2017 Oscars Pop critic resources Lifetime MSNBC BBC independent ViacomCBS CW Seed Spring TV TCA south america Unbreakable Kimmy Schmidt comic book movies Pop TV Hulu Marvel Sundance Now posters rt labs critics edition Nat Geo joker toy story GIFs Schedule travel IFC comic trophy fast and furious french Musicals 45 Black Mirror X-Men game of thrones die hard IFC Films BET Amazon superman mockumentary Travel Channel Lifetime Christmas movies Acorn TV The Arrangement Crackle Netflix mission: impossible rom-coms live event Britbox blaxploitation name the review Comic-Con@Home 2021 HFPA Summer Wes Anderson italian Heroines binge blockbusters marvel comics quibi live action New York Comic Con biopic Paramount Network adaptation deadpool 20th Century Fox halloween tv comic books comedies reviews NBA Fox Searchlight kong game show crime Year in Review cops Amazon Prime Video what to watch spider-man Masterpiece romantic comedy Shondaland 72 Emmy Awards cults dceu HBO Go MCU sopranos Mary poppins spanish royal family boxoffice Exclusive Video psychological thriller Television Academy child's play video on demand Logo TCA Awards social media diversity action-comedy Infographic stand-up comedy LGBTQ stop motion Lucasfilm cars marvel cinematic universe MTV teaser Comedy Central crime thriller asian-american Tumblr golden globes indie Sundance concert PlayStation YouTube Red VH1 Certified Fresh war robots serial killer batman TBS Tokyo Olympics WarnerMedia christmas movies satire Avengers E3 AMC Emmy Nominations Red Carpet TNT Trophy Talk talk show dc GoT Set visit Extras award winner jurassic park Endgame 79th Golden Globes Awards saw hispanic heritage month nature werewolf ITV FXX Interview DC Universe The Purge Teen Showtime indiana jones Marvel Television