Oscars flashback: 5 reasons why Sean Penn won Best Actor for ‘Mystic River’

We had no idea what we were in for. Allow me to backtrack just a bit.

Three-time previous nominee Sean Penn had taken an early lead for his role as a troubled ex-convict and grieving father in Clint Eastwood’s crime drama “Mystic River.” Then Bill Murray began to generate major buzz for his portrayal of an aging movie star in Sofia Coppola’s acclaimed Tokyo-set comedy “Lost in Translation.”

The Golden Globes did little to clarify things. Penn prevailed in the drama category while Murray picked up the comedy/musical award. The latter did arguably get a bit of a boost with his charming acceptance speech. (Penn was a no-show, and Eastwood awkwardly attempted to thank the Globes on his actor’s behalf.)

All eyes were then on the Screen Actors Guild Award, which many thought would serve as a tie-breaker. But in the ultimate awards twist, the prize went to Johnny Depp for bringing the colorful and crafty pirate Jack Sparrow to life in the summer’s swashbuckler smash “Pirates of the Caribbean: The Curse of the Black Pearl.”

Suddenly, the contest was even more exciting than most observers had anticipated. Did Depp’s surprise at SAG foretell an Oscar upset? Had his “Pirate” suddenly placed a “Curse” on Penn and Murray? (Reminder: all three had made Oscar’s Best Actor lineup, along with Ben Kingsley in “House of Sand and Fog” and Jude Law in “Cold Mountain.”)

Oddsmakers were almost evenly split between Penn and Murray going into Oscar night, and most recognized that Depp was a very real threat. But when 2002’s Best Actress for “The Hours” Nicole Kidman opened the envelope, it was Penn’s name that was penned on the card.

Fortunately, the actor made the decision to attend the ceremony (after ignoring his first three invites) — and received a thunderous standing ovation. So how did Penn do it? Here are my five reasons why.

1. He had the most serious and dramatic role.
The academy has long been reluctant to reward comedic performances, especially in the lead categories. While Murray’s skillful and nuanced work in “Lost in Translation” was superb, the part didn’t quite have the same gravitas as Penn’s character, ex-convict James “Jimmy” Markum. And as delightful as Depp was in “Pirates,” his Captain Jack was perhaps sailing in waters too shallow for the tastes of those sophisticated voters. That allowed Penn to hit the Oscar jackpot.

2. He had the killer scene.
It seems silly to say “spoiler alert” for a 20-year-old film, so I won’t. (But you’ve been warned.) The moment that his character realizes that his daughter has died, Penn exhibited the type of over-the-top acting that voters eat up. The agony. The intensity. The impact. I have a feeling that most academy members had that scene in mind as they marked Penn’s name on their ballots.

3. He was seen as the most due for the Academy Award.
“Mystic River” gave Penn his fourth shot at Best Actor. He had previously contended for 1995’s “Dead Man Walking,” 1999’s “Sweet and Lowdown” and 2001’s “I Am Sam.” It would have been hard for the academy to deny him again, especially in favor of first-time nominees Murray and Depp – who weren’t deemed undeniable for their projects.

4. “Mystic River” had more overall academy support than “Lost in Translation” and “Pirates of the Caribbean.”
Penn’s film has six noms, including Best Picture, Best Director for Eastwood, Best Supporting Actor for Tim Robbins, Best Supporting Actress for Marcia Gay Harden and Best Adapted Screenplay. (Robbins stole the prize in his category, the only other Oscar for “Mystic River.”) “Lost in Translation” was similarly a Best Picture nominee, but with just four bids (including Best Director and Best Original Screenplay — the latter of which would be the only win for “Lost”). As for “Pirates,” Depp was the only above-the-line nom of its five, which put him in rough waters. The momentum for “Mystic River” meant smooth sailing for Penn.

5. He received bonus points for “21 Grams.”
I’ll concede that this was only a small factor, but might have made a big difference in a tough contest. Penn presented a much more subdued turn as a dying professor in “Grams.” But the heavyweight dramatics of Naomi Watts and Benicio Del Toro earned them nominations for Best Actress and Best Supporting Actor, respectively. Most academy members probably watched the film, and were impressed by Penn’s body of work in 2003. The combined weight of his starring roles in both “Mystic River” and “21 Grams” tipped the scale in his favor. Twenty years later, it all adds up.

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