10 Top Sean Penn Movie Quotes: ‘Milk,’ ‘Mystic River,’ ‘Fast Times at Ridgemont High’ (Video)

The two-time Oscar winner doesn’t say much in action-packed “Gunman,” but these lines are classics

Last Updated: March 21, 2015 @ 11:04 AM

TheWrap introduces a fun new series of sorts, picking actors’ Top 10 movie quotes. What are the famous lines that fans will quote decades from now and that these actors will be remembered by?

We’re kicking off the weekly trip down memory lane with Sean Penn, who co-wrote and stars in the international action-thriller “The Gunman,” which opens Friday. Penn is the rare movie star who may be more quotable in real life than on the big screen, but regardless, we had to make some hard choices.

There were some tough omissions from “Carlito’s Way,” 21 Grams,” “Sweet and Lowdown” and Penn’s early hit “Bad Boys,” but in the end, we were limited to 10 quotes from 10 different movies, not counting our exceptionally quotable top choice.

If there’s a line we missed, let us know in the comments section below. And if you haven’t seen some of these movies, be sure to catch up on Penn’s catalogue of classics.

1. (tie): MILK - “You gotta give ‘em hope” & “I know you’re angry! I’m angry!”

Penn won his second Oscar for his heartbreaking performance as iconic gay rights activist Harvey Milk in Gus Van Sant’s drama, which also won an Oscar for its original screenplay written by Dustin Lance Black. As a crusader for change, Milk’s powerful speeches gave Penn plenty of opportunities to shine.

2. MYSTIC RIVER – “Is that my daughter in there?”

Penn won his first Oscar for his devastating performance as an ex-con whose daughter is brutally murdered. Penn conveys appropriate grief as a shattered father desperate for revenge. And his Boston accent isn’t half bad either.

3. THE THIN RED LINE – “What difference do you think you can make, one man in all this madness?”

There’s a certain poetry to Terrence Malick’s screenplays, and this three-hour war drama allows Penn to recite philosophical dialogue about men and war and other macho themes in a hushed, haunted tone that would make Hemingway smile.

4. FAST TIMES AT RIDGEMONT HIGH – “You dick!”

Jeff Spicoli is one of Penn’s earliest and most famous characters, but the perpetually-stoned surfer didn’t really have a signature phrase of dialogue. While this selection narrowly beat out “Aloha, Mr. Hand,” his line delivery here is too perfect to overlook.

Editor’s Pick for Honorable Mention: The Pizza Delivery Scene – “If I’M here and YOU’RE here doesn’t that make it OUR time?”

5.  DEAD MAN WALKING – “Thank you for loving me.”

Penn earned his first Oscar nomination for playing Matthew Poncelet, a death row inmate who strikes up a special friendship with a nun, played by Susan Sarandon. Penn’s powerhouse performance helps us sympathize with a murderer, a pretty impressive feat.

6. I AM SAM – “You don’t know what it’s like when you try, and you try, and you try, and you try, and you don’t ever get there!”

Penn earned his third Oscar nomination for this tearjerker about a man with a developmental disability who must care for precocious 7-year-old daughter, played by Dakota Fanning. Penn tackles a challenging role with grace and humanity, and some of his scenes with Michelle Pfeiffer sparkle.

7. THE GAME – “What do you get for the man who has everything?”

In one of his best supporting turns, Penn plays Michael Douglas‘ younger brother in David Fincher’s twisted thriller. Penn constantly keeps the audience guessing and despite a 16-year age gap with Douglas, the duo muster solid chemistry as estranged siblings.

8. CASUALTIES OF WAR – “This is a weapon, this is a gun. This is for fighting, this is for fun.”

Penn stood out as Sergeant Tony Meserve, a troubled soldier who orders his unit to kidnap a Vietnamese girl to be their sex slave and ostracize Max Erikkson (Michael J. Fox) when he expresses reservations. Penn’s performance inspired his co-stars to bring their A-games to Brian De Palma’s 1989 drama.

9. THIS MUST BE THE PLACE – “I’m not trying to find myself. I’m in New Mexico, not India.”

Penn does a great Robert Smith impression as a bored rock star tracking down a former Nazi who persecuted his father during the Holocaust. Despite the loud hair and makeup, it’s a low-key turn for Penn, who deftly balances humor and pathos.

10. GANGSTER SQUAD - “Back East I was a gangster; out here, I’m God.”

Penn may have chewed up all of the Los Angeles scenery in Ruben Fleischer’s period movie, but he was also the film’s heart and soul as bad-ass crime boss Mickey Cohen, who seems to always have a zinger at the ready.

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