With the 87th Academy Awards set to take place Feb. 22, Hollywood is busy readying itself for one of the most glamorous nights of the year when filmmakers and stars gather to honor the best and brightest in the industry.

But which way the Academy will vote is never entirely predictable, and the history of the Oscars is full of wins that, particularly in retrospect, may be surprising.

With the benefit of hindsight, here’s a look at just a few of the surprising, and occasionally puzzling, wins in Academy Award history.

1941 — “How Green Was My Valley” beats “Citizen Kane”

John Ford’s 1941 film about a family of coal miners in turn-of-the-century Wales won five Oscars all together, including Best Cinematography, Best Director and Best Picture.

In four of those categories, though, Ford’s film beat out what is widely regarded as possibly the greatest American film ever made, Orson Welles’ “Citizen Kane.”

The results of the 1941 Oscars aren’t just a case of “hindsight is 20/20,” though.

“Citizen Kane” had already collected major accolades, and early expectations were that it would sweep the awards — that is, until newspaper magnate William Randolph Hearst stepped in. Hearst launched a smear campaign unlike anything else in Oscar history that included threats of blackmail and FBI investigations, and it worked.

The night of the Academy Awards, the audience booed every time “Citizen Kane” was mentioned, and Welles walked away with only one award for writing.

1956 — Yul Brynner beats a who’s-who of acclaimed actors

Having previously only appeared in a few TV shows and one B-movie, 1956 was a big year for Brynner.

The Russian-born actor managed to snag star-making roles as Rameses opposite Charlton Heston’s Moses in “The Ten Commandments” and as a love interest to Ingrid Bergman’s titular Russian aristocrat in “Anastasia.” But it was his iconic performance as King Mongkut of Siam in “The King and I” that won him an Oscar for Best Actor.

In retrospect, that might not seem all that surprising until one considers Brynner’s fellow nominees, which included Rock Hudson, Kirk Douglas, Sir Laurence Olivier and, posthumously, James Dean in his final screen performance.

No matter who the actor is, that’s some pretty stiff competition, making Brynner’s win all the more surprising.

1958 — Hugh Griffith beats George C. Scott, Stephen Boyd

In 1958, “Ben-Hur” famously set the record for most Oscars with an impressive 11 wins, including Best Director for William Wyler and Best Picture. That number has since been matched on two separate occasions (first by “Titanic,” then “The Return of the King”), but it’s never been beaten, and there’s a good chance it never will be.

Looking back, though, at least one of “Ben-Hur’s" awards might surprise modern audiences watching the film, namely Hugh Griffith’s win for Best Supporting Actor playing the Arab Sheik Ilderim.

Although not a bad performance, Sheik Ilderim is basically just comic relief, and especially by today’s politically correct standards, the character smacks a little bit too strongly of Arab stereotypes.

Among the actors Griffith beat out was George C. Scott, whose role as the cynical prosecuting attorney in “Anatomy of a Murder” seems like a more obvious choice for Oscar gold.

More egregiously, though, Griffith’s nomination came at the expense of his “Ben-Hur” co-star Stephen Boyd, who played the villainous Messala. Boyd had already won a Golden Globe for the same role, but apparently his depiction of a smarmy Roman centurion was too unlikable to even get him nominated by the Academy.

1981 — Vangelis beats John Williams

Mention “Chariots of Fire” to your average movie fan, and they’ll immediately start humming Vangelis’ memorable, synth-heavy anthem (and depending on the level of fan, possibly break out into a slow-motion run).

The Greek composer, who also did the music for films like “Blade Runner,” managed to craft what is undeniably one of the most iconic scores ever put to film.

But in 1981, Vangelis’ pioneering electronic soundtrack, which comes across as painfully dated nowadays, somehow managed to beat out perennial Oscar favorite John Williams at the absolute top of his game. After all, 1981 was also the year Williams was nominated for “Raiders of the Lost Ark.”

Williams’ subsequent work on “Indiana Jones and the Temple of Doom” in 1984 and “Indiana Jones and the Last Crusade” in 1989 was also nominated, but they lost to “A Passage to India” and “The Little Mermaid,” respectively, meaning that Williams never won an Oscar for what is arguably some of his best scoring after “Star Wars.”

As classic as “Chariots of Fire” is, in retrospect, that seems like a mistake.

1992 — Marisa Tomei beats Miranda Richardson, Vanessa Redgrave

Marisa Tomei’s Best Supporting Actress award for “My Cousin Vinny” has gone down as possibly the most head-scratching win in Oscar history.

Nominated against seasoned actresses like Miranda Richardson (“Damage”) and Vanessa Redgrave (“Howards End”), who appeared in far meatier roles, nobody expected Tomei to stand a chance, let alone walk away with a statue.

Her win is so puzzling, in fact, that a rumor has persisted for years that her name was read by mistake.

To her credit, though, Tomei has gone on to demonstrate Oscar-caliber acting chops throughout her career, and since “My Cousin Vinny,” she has been nominated two more times for “In the Bedroom” and “The Wrestler.”

1998 — “Shakespeare in Love” beats “Saving Private Ryan,” Cate Blanchett

In 1998, Steven Spielberg took home his second Academy Award as a director for “Saving Private Ryan,” but to the surprise of many, lost Best Picture to “Shakespeare in Love.”

Looking back, it’s hard to imagine how a comparatively slight romantic comedy — even one set in Elizabethan England — managed to outdo a Spielberg war epic starring Tom Hanks, but there must have been something in the water. In another upset, “Shakespeare in Love” also scored its star Gwyneth Paltrow the Best Actress award that many expected would go to Cate Blanchett for her powerhouse portrayal of Queen Elizabeth I in “Elizabeth.”

2006 — Martin Scorsese beats his own bad luck

Few names carry as much clout in modern American cinema as Martin Scorsese. The filmmaker behind classics like “Mean Streets,” “Taxi Driver,” “Raging Bull” and “Goodfellas” helped define a new Hollywood in the 1970s that championed the role of the director above studios.

But it took Scorsese six nominations spread across three-and-a-half decades to finally win a Best Director award.

After so many near-wins, it had begun to feel like Scorsese would join the ranks of directors like Ingmar Bergman, Alfred Hitchcock and Akira Kurosawa who never won an Oscar.

In 2006, though, Scorsese was finally recognized by the Academy for his gritty crime drama “The Departed,” which also won Best Picture.