All careers, even the great ones, have their ups and downs. Michael Jordan had his Wizards run. Shaq spent a year with the Celtics. Tiger Woods has his entire life right now. Our legends are fallible, but they don’t become legends without the sort of dizzying heights of success we mere mortals can only dream about. A great man once said that life is a highway, and if you really are gonna ride it all night long, you might get a flat tire or two in the process.

Sean Penn is many things — gifted actor, humanitarian, party pooper, and troubled man who has been charged with felony domestic assault. He has done some of the best and worst acting of the last 30 years. With the release of The Gunman, we look back at Penn’s roles, and we asked the intrepid Grantland staff to pinpoint the exact moments we were blessed with Peak Sean Penn, and when we were bludgeoned with Valley Sean Penn.

Peak — Bad Boys

Bill Simmons: I remember sleeping over at a buddy’s house in eighth grade, during the primitive days of cable TV and VCRs, when he told me, “My dad has a VHS tape of Bad Boys!”

Bad Boys? That was just in the movie theater! And it’s rated R! And we can watch it right here????

I couldn’t believe it. I remembered seeing the commercials and knew Sean Penn was in it, but that was all I knew. Penn had gained acclaim for his performances in Taps (which I had seen) and Fast Times at Ridgemont High (which I wasn’t allowed to see). There were enough promising young actors back then — Penn, Timothy Hutton, Tom Cruise, Rob Lowe, Matt Dillon, Patrick Swayze, Matthew Broderick — that everyone kept hyping how many promising young actors there were. Francis Ford Coppola had cast many of them in The Outsiders, a heavily promoted movie that came out the same day that Bad Boys was released. So we knew about Penn, we just didn’t know about him. And then, we watched Bad Boys.

Penn played Mick O’Brien, a Chicago street thug who accidentally murders a gangbanger’s little brother as he frantically drives away from a botched robbery. They actually made Mick’s character too unlikable — there’s nothing redeeming about him, except for the fact that Penn played him, of course. It’s my favorite Penn performance, the movie-star version of the spectacular season that Anthony Davis is having right now. Great in the moment … but headed for bigger and better things, too. He owns every single scene. He’s brooding and calculating and violent and compelling and strangely likable, even though you can’t figure out why.

Once Mick lands in juvie, you root for him the entire time — even though the movie starts with him viciously mugging some innocent Chicago man, and even though he’s already pancaked some little kid with his car. It’s the kind of part that no young star would have the balls to play anymore. Make this guy likable even though he isn’t. Later in the movie, the grieving gangbanger (Paco, played by Esai Morales) ends up in the same juvie prison after vengefully assaulting Mick’s girlfriend. The last 40 minutes morph into a Mayweather-Pacquiao scenario, as Paco and Mick circle each other for their inevitable fight to the death. It’s so inevitable that everyone in juvie starts betting on one or the other. I can’t remember a cleaner, smarter premise for a climactic movie brawl.

But by that point, Penn had already peaked in the movie — in the unforgettable scene when the two “alpha dogs” in juvie, Tweety and Viking, decide to take him out. Do they want to beat him up or sexually assault him? It’s unclear. Mick sniffs out their plan, walking over to the soda machine as his menacing bullies follow from afar. He purchases four sodas, hauls them back to his room, throws them in a pillow case and tells his roommate to leave. What follows is one of the great moments of Penn’s career. I remember watching that scene with my buddy, screaming in delight, then making him rewind it and devouring it again. We couldn’t believe it. Maybe Sean Penn’s actual career never matched the immense potential that he flashed in Bad Boys and especially in that scene, but I guess he came close enough.

Peak — The Falcon and the Snowman

Charles P. Pierce: In addition to having one of the coolest Bowie tracks ever on the soundtrack, The Falcon and the Snowman is a wonderful vehicle in which to watch Sean Penn’s eyeballs spin counterclockwise until they seem to be ready to pop right out of his head. The story, of course, involves Christopher Boyce (played by Timothy Hutton), an employee working on a highly classified spy satellite program who gets disillusioned and starts selling secrets to the Russians. Penn is Andrew Daulton Lee, a friend of Boyce and fellow onetime altar boy, and an extraordinarily maladroit drug smuggler. Boyce enlists Lee to be the courier between himself and the Soviet embassy in Mexico. Lee is half-mad to begin with and pole-vaults into pure crazy under the pressure of what he and Boyce are doing. Here he is, dickering with their Soviet handlers as though he were buying a used Buick at Bugtussle Automotive. (Through most of the movie, he’s rocking a pencil-thin 1970s porn ’stache, but that seems to have disappeared in the late going. The period-piece fake leather jacket is adorable, though.) This is what happens when Jeff Spicoli meets James Bond — James Bond never has a chance.

Valley — Mystic River

Dan Fierman: I’m a Boston guy who has a Boston guy for a boss, and this is based on Dennis Lehane’s greatest Boston novel. I get it. I’m supposed to rep for this movie. But let’s be honest: It’s an overwrought, only OK film with the worst regional accents this side of Blown Away or Julianne Moore’s ill-advised turn on 30 Rock.

But putting aside all of that, Mystic River is absolutely everything that’s wrong with Sean Penn: capital-A-Acting dialed up to the highest possible level. His signature menace not simmering under the surface, but boiling up and spilling all over the stove and making an unholy mess. Screaming. Yelling. Rending of garments. That statue of a face contorted into a self-parodic storm of grief and fury. It’s no surprise at all that Penn won his first Oscar for this performance. But for folks who like him understated and quietly dangerous, it was a little like giving an ostrich an Uzi: something that seems like a fun idea at the time, but only encourages bad behavior.

Peak — Carlito’s Way

Chris Ryan: Here’s the secret about Sean Penn: great actor, bad movie star. He does his best work when he is freed from carrying a film. Such are his talents, and the demands of Hollywood stardom, that we rarely see him riding shotgun — he’s always driving the car, 50 mph, straight into the Method brick wall. Up until 1993, it looked like his entire career was going to be some variation on this scene from State of Grace.

Turns out, all Sean Penn needed was to be paired with a bigger ham than he was. In Carlito’s Way, he shares the screen with noted Puerto Rican thespian Al Pacino. Penn plays Dave Kleinfeld, the lawyer for Pacino’s reformed gangster, Carlito Brigante. Every choice Penn makes — from Kleinfeld’s suits to his cocaine confidence, his faux-cool demeanor (remember the scene in which he hums a cop-show theme song to the district attorney?), his thinning fro, and his cigarillos — is inspired. An entire film about Kleinfeld would have grated — it would have played like Emmet Ray, Attorney at Law. But as comic relief, as muckraker, as a kind of Iago to Pacino’s Othello, Penn is perfect. His gestures have the maximum amount of impact in the minimum amount of screen time. The Less Is More horse left Stella Adler’s Method barn a long time ago, but it’s a shame Penn hasn’t spent less time onscreen over the course of his career. His name shines brighter below the line.

Valley — Gangster Squad

Holly Anderson: Gangster Squad is not a good movie, and is populated wall to wall with actors who either (a) didn’t read the script or (b) were actually just kids masquerading as adults in trench coats this entire time, and who decided to put on a play for Parents Day at their daycare center. There is no in-between justification for everybody involved not knowing better.

In this scenario, Penn is the kid who has to stay in the house with an ear infection while everybody else hung up sheets for stage curtains on the patio. As the movie’s big bad, he’s offscreen for a lot of it while Josh Brolin’s titular unit of cops is mowing swaths through less important mobsters — all, LOOKIT A TOMMY GUN YEEHAW BLAMMO. Here is an actual speech Penn has to make, with a straight face:

Whores don’t grow on trees.They’re like mustangs. You gotta catch ’em wild and break ’em before you train them to do tricks. Means I need a quiet place where I can keep the girls locked up, keep them hopped up on Mexican dope. But this cop comes out of nowhere like an early frost. And now my whole crop of cunt is ruined.

Maybe the only fun he gets to have the entire time is yelling, “Here comes Santy Claus!” at the very end, before shooting up a bunch of potted poinsettias and heading off to prison. Sorry, man. Even you deserved better than this.

Peak — Fast Times at Ridgemont High

Mark Lisanti: This might be a controversial thing to say about a man with a 34-year movie career, but Sean Penn’s earliest peak remains his highest. Yes, he has Best Actor Oscars for Milk and the (bafflingly overrated) Mystic River. Yes, he has the three other nominations for Dead Man Walking, Sweet and Lowdown, and [uncontrollable coughing fit] I Am Sam. Yes, he has the hair in Carlito’s Way and the soda cans in Bad Boys. But nothing he’s done since he first exploded into — OK, “exploded into” is not quite right; how about “strutted toward, a half hour late, carrying a slice of pepperoni pizza” — the public consciousness in Fast Times at Ridgemont High in 1982 has topped his breakout as Jeff Spicoli, the most important stoner/surfer in cinematic history. Spicoli is Penn at maximum likability and minimum self-seriousness, a fledgling golden god unencumbered by the knowledge that his blunted smirk would soon be inverted into a permanent, De Niro–quality grimace¹ or that he’d develop into a classic son of a bitch with a lifetime enthusiasm for cold-cocking paparazzi.

But let’s not use this space to lament the furrowed-brow sourpuss Penn would become — let’s celebrate the checkered-Vans-wearing, squinty-eyed devourer of tasty waves we first fell in love with. The one who clashed, over and over again, with the outstretched hand² of authority. The one who coughed, “You dick!” into the face of his U.S. history teacher like an unsuppressable lungful of bong smoke.

Peak — All of 1997

Sean Fennessey: Fresh off his first Academy Award nomination for 1995’s Dead Man Walking, Sean Penn set about on the most productive period in his career: eight films in three years, including five parts in 1997. And here’s the power of Sean Penn in ’97:

I’m not referring to Penn’s broken baby-man performance in Nick Cassavetes’s She’s So Lovely, but to his character Eddie Quinn’s unintentional plot synopsis of The Curious Case of Benjamin Button, 11 years before the latter movie’s release. Aging backwards, that’s what Penn could do back then, transform into all kinds of men, with more influence to green-light a movie than is conceivable now. He was a movie star in the old-fashioned sense, like Burt Lancaster in the ’50s and ’60s, who sought out his favorite filmmakers and then forced them into his vision of masculinity. In short order, Penn was a wounded and clairvoyant simp, as in Lovely; an arrogant hotshot who drifted into a noir nightmare Arizona town (Oliver Stone’s cockeyed U Turn); and a slyly malevolent sibling engineering the darkest birthday present imaginable (David Fincher’s The Game). He showed up in a late-period head-scratcher from a counterculture genius (Robert Downey Sr.’s Hugo Pool), an acid-drenched adaptation of David Rabe’s burn-Hollywood-burn play Hurlyburly, and he shot several long, opaque sequences in the sun-dappled magic hour astride a U-boat, many of which never appeared in the final version of Terrence Malick’s The Thin Red Line, which was released in 1998.

He always worked with interesting filmmakers and writers — Lovely was the last unproduced work from the late John Cassavetes — and even at his twitchiest and most snively, he commanded with a kind of slack gravitas. U Turn is one of the least remembered and least accessible movies from this period, but it is a master class in the kind of live-wire malaise performing style that actors like Joaquin Phoenix, Laura Linney, Philip Seymour Hoffman, and Alison Pill have adopted: pure motormouthed adrenaline one minute; lackadaisical, existential woe the next. Penn went on to greater success and greater failure in the ensuing decades, slowly corroding into a leathery, self-serious shell of himself. But coked up or cooled down, stressed out or reeled in, during this run, he was as unpredictable and gripping as he’d ever be.

Valley — 2005 Academy Awards

Steven Hyden: I used to love Sean Penn. Spicoli is one of my all-time favorite movie characters. He was an excellent weasel in The Falcon and the Snowman and Carlito’s Way. I saw U Turn on opening weekend, for crying out loud. Then this happened.

This is Penn at the 2005 Academy Awards, presenting the award for Best Actress. “Forgive my compromised sense of humor,” he begins, “but I did want to answer our host’s question, about who Jude Law is.” The “question” was a harmless bit about Law starring in a million movies in 2004. (Actually, it was six. Six is a lot.) This is the sort of thing “our host” is supposed to do, especially if “our host” is Chris Rock. Here’s a tip: If Chris Rock makes fun of your friend, take it as an honor. It’s Chris Rock, man!

Sean Penn did not take it as an honor.

“He’s one of our finest actors,” he says, prompting the most pained slow-clap ever. Ugh. Look, I always assumed that Penn was probably a prick in real life. But this display of peak smugness brought it into my living room. It turned me off, and the switch has stayed off ever since. “Forgive my compromised sense of humor” is the sad, humorless bookend to “Hey, bud, let’s party!”

Peak — Casualties of War

Sean Witzke: In any other Vietnam movie, Sgt. Tony Meserve is a cautionary tale. He’s Lieutenant Dan or Animal Mother — the soldier who has learned the harsh realities of his situation and is behaving accordingly. He’s a good man in an impossible situation. He may do evil shit, but that’s combat. Casualties of War is a Brian De Palma movie, so Meserve starts off as a tragic hero. He saves lives, he shoots the enemy, he consoles a best friend who is bleeding to death. Then we watch as those experiences transform him into a war criminal, a rapist, and a murderer. By the end, he’s pure evil. (Penn’s role in Malick’s Thin Red Line is an extension of Meserve — a much less venal man whose soul has been destroyed by war.)

A lot of the showy, Method posturing crap that grates about Penn works in this role. He apparently wouldn’t spend time with Michael J. Fox on set, to increase tension. Instead, Penn hung with the Army consultants. But maybe Penn wasn’t that far off from the character: super young, well trained, violent, a piece of shit toward women, not really that smart. Again and again, the film points out that this guy is stupid — based on how he talks. But somehow, it doesn’t cheapen the character. It just makes him scarier.

Peak — The Assassination of Richard Nixon

Kevin Lincoln: In 2004, having spent the last two years hoovering accolades for 21 Grams and Mystic River, Sean Penn decided it was time to really become Robert De Niro. He did this by making The Assassination of Richard Nixon, based on the true story of Samuel Byck, a mentally ill tire salesman who attempted to hijack a plane and crash it into the White House. Spoiler alert: Sean Penn attempts to hijack a plane and crash it into the White House. First, though, he does some acting, so steeped in masochism and self-deprecation that it couldn’t have been a more blatant play for hardware if he’d been calling out for Oscar in his sleep.

This isn’t to say he’s bad; critics praised the actor while generally golf-clapping the film, which grossed less than $1 million. But watching The Assassination of Richard Nixon on DVD with my parents, I saw Penn as being at the apex of acting, a warrior, a sufferer-king. While Penn’s accomplishments are legion, his most emblematic laurel will forever be dazzling a 14-year-old boy, the silliest of all creatures, particularly as long as he continues behaving like a 14-year-old boy himself.

Peak — Sweet and Lowdown

Amos Barshad: On the Concourse this week, Will Leitch wrote about the dourness of Sean Penn:

It’s as if [Spicoli] embarrassed him so much that he spent the next 30 years making certain we found him a humorless bore in every way possible. There were some great performances during that time, no doubt, but all rooted in that overpowering, often oppressive self-seriousness: Penn desperately wanted us to know that he had demons, man.

This is fundamentally true, and upsetting, with the only really major exception being Woody Allen’s 2000 jazz guitar comedy Sweet and Lowdown. In it, Penn’s a dick, but a funny, weird, sweet one. There are affectations galore, so it’s no less actorly than anything else he’s ever done, but it’s a rare treat to see him point all that considerable skill toward cutting himself down. I miss that Penn.

On an only vaguely related note: At some point in the last few years, my brother and I started telling people that Sean Penn’s birth name was “Sean Pawn,” but that he had to change it to Sean Penn because he couldn’t get any parts with a name like Sean Pawn. It’s a helpful thing, I promise: Start referring to him as Sean Pawn, and our man feels suddenly, magically just a scooch or two less sad.

Valley — I Am Sam

Dave Schilling: No Academy Award–nominated role has been more derided, more disrespected, and more maligned in recent memory. So many prestige movies are instantly forgotten after awards season concludes (Does anyone ever watch Atonement or Albert Nobbs for fun?), but I Am Sam is still talked about by pundits and the general public despite having a 34 percent rating on Rotten Tomatoes and a reputation for being a manipulative mess. I Am Sam endures because of how jaw-droppingly unsubtle Sean Penn is in it. You know that “full retard” speech from Tropic Thunder?

It ends with a reference to I Am Sam because that movie is one of the most potent examples of an actor’s undying commitment to excess.

Penn plays Sam Dawson, a man described as possessing the “mind of a 7-year-old” who fights the government to keep custody of his daughter. Because Sam has a developmental disability, he’s considered incapable of caring for a child who is rapidly outgrowing his ability to protect her.

To his credit, Sean Penn commits fully to the role. It could have been so easy for his work to devolve into an offensive caricature or something as cloying and irritating as Giovanni Ribisi and Juliette Lewis in The Other Sister. I don’t think he’s goofing off in this movie. An actor who takes his craft as seriously as Penn would not be expected to offer anything less. The problem is that it’s Sean fucking Penn in this movie. I truly don’t believe I am the only one who finds it impossible to dissociate myself from the reality that movie star and notorious hothead Sean Penn is attempting to recreate the effects of a developmental disability. Sorry, but Mr. Penn is not a chameleon. He does not “disappear” into a role. This is the movie star’s curse — no matter who you play, you’re still you. I don’t care if he’s playing a working-class Boston dad, Harvey Milk, or gangster Mickey Cohen. I just never, ever, ever buy it. Plus, he’s one of the least restrained actors we have. When he’s given physical ticks, accents, or wacky props to play with, it’s like locking a 15-year-old in a room with a Slurpee machine and a box of old pornography — he’s going to make a mess that no one wants to clean up.

Penn’s favorite acting trick is YELLING A LOT, and in I Am Sam he YELLS A LOT. All the crying and the screaming and the wild gesticulating overwhelms me to the point where I become legitimately uncomfortable and want to watch anything else. Perhaps that’s his gift: to wring an emotional reaction out of you by any means necessary. I have seen I Am Sam more than once, and it is the saddest movie I’ve had to endure that’s not a Hallmark Original Movie. It has one fucking mission and that is to make you cry. Somehow, I find myself rooting for the completely irresponsible idea that Sam should continue to have sole custody of his daughter every time. He physically, mentally cannot and should not do it, but I fall for him whenever those courtroom scenes get going. Make no mistake, this is not a good movie, but it does inspire me to want to call my mom and tell her I love her. I guess that’s something, but that doesn’t mean it’s not also the low point in a very bizarre career.

1. If Penn learned that from him during their We’re No Angels downtime, that’s just another sin for Bobby to answer for.

2. Pun intentional, unconscionable.