With the 2017 awards season quickly approaching, it's always fun to look back at previous years and reflect on which actors have taken home the most coveted award in Hollywood - the Academy Award.
However, not every actor who has managed to bring home an #Oscar struck gold overnight. Most Oscar winners have long resumes to go along with their statue. It's not uncommon for a winner to have a long list of previous nominations or snubs.
Here are five Oscar winners who by all accounts should have taken home a statue before they actually did. Whether it was a failed nomination, a race that was just too close, a dark horse opponent, or a blatant snub, they showed us just how difficult the journey towards the highest honor can be.
1. Heath Ledger
What he won for: Best Supporting Actor, The Dark Knight (2008)
When he should have won: Brokeback Mountain (2005)
Heath Ledger's Oscar win came shortly after his untimely passing on January 22, 2008. The Academy honored him for his role as the groundbreaking, anarchist version of #TheJoker in Christopher Nolan's The Dark Knight. Despite how well-deserved the posthumous award was, it is extremely difficult to ignore one role that hit just four years prior, where he starred opposite Jake Gyllenhaal as a closeted gay cowboy.
Brokeback Mountain was groundbreaking in the sense that it showed a relationship between two men at a time when LGBT rights weren't nearly as accepted culturally, or in Hollywood, as they are today. No matter how great Ledger's performance as the Joker was (and it really was great), there is no denying the fact that his first Oscar win should have come from his role as Ennis in Brokeback Mountain.
2. Julia Roberts
What she won for: Best Actress, Erin Brockovich (2000)
When she should have won: Pretty Woman (1990)
There's no question that #JuliaRoberts deserved to win Best Actress for her real-life role of environmental activist Erin Brockovich. Roberts elevated her talents and easily proved that she was Oscar material. However, there is one other role in which she showed her talents that (in my opinion) should have been her first Oscar.
Roberts' portrayal of a prostitute hired by a wealthy businessman may not sound like Oscar bait, but the performance as Vivian Ward proved Roberts as a Hollywood powerhouse in 1990. After all, Pretty Woman was her first Oscar nomination in 1991 and influenced future collaborations between her and Richard Gere.
It's a shame that she didn't win an award for this amazing role, but luckily it sparked a longtime career on the big screen.
3. Jared Leto
What he won for: Best Supporting Actor, Dallas Buyers Club (2013)
When he should have won: Chapter 27 (2007)
#JaredLeto managed to take home an Oscar for his role as a transgender woman with AIDS in Dallas Buyers Club. But should the role of Rayon have been his first award?
Leto's capability to transform into just about anyone was most recently seen with his portrayal of the Joker in #SuicideSquad, but it was previously showcased when he transformed into Mark David Chapman, the man who assassinated John Lennon in 1980. In addition to gaining 67 pounds — and suffering serious health issues as a result — Leto managed to tackle the portrayal of Chapman's mental illness in a way that most actors wouldn't have been able to pull off.
Chapter 27 unfortunately didn't gain much acclaim past its Sundance Film Festival debut in 2007, but that doesn't mean Leto wouldn't have deserved any recognition for his performance.
4. Leonardo DiCaprio
What he won for: Best Actor, The Revenant (2015)
When he should have won: What's Eating Gilbert Grape (1993), Titanic (1997), Revolutionary Road (2008), Inception (2010), Django Unchained (2012) and/or The Wolf of Wall Street (2013)
After four nominations (and several snubs), it became a running joke on the internet: when is #LeonardoDiCaprio going to win an Oscar? Nonetheless, DiCaprio completely slayed his competition in 2016 and managed to finally win a statue for Best Actor for The Revenant in 2016. Although there's no denying that his performance as Hugh Glass was deserving of the statue, it was by no means the first Oscar-worthy performance he delivered.
There were so many missed opportunities for Leo to win, but personally I most wanted to see him bring home the Oscar for The Wolf of Wall Street. DiCaprio's performance as the real-life Wall Street mogul Jordan Belfort was utterly brilliant.
It was obvious how much he put into the performance, and the character's rags-to-riches transformation was almost painful to watch at times. Add in the arrogant humor that only DiCaprio could have ever been able to pull off, and you have a performance that should have easily had him up on that stage for the first time. He just couldn't beat the unstoppable Matthew McConaughey!
5. Natalie Portman
What she won for: Best Actress, Black Swan (2010)
When she should have won: Closer (2004) and/or Garden State (2005)
Despite the amount of powerhouse performances that #NataliePortman has given throughout her career (and her most recent work as Jackie Kennedy in #Jackie), it's somewhat surprising that her only Oscar came from the role of a troubled ballerina in Black Swan.
The 2010 film showcased Portman's ability to transform into a role and become a completely different person both physically and mentally. However, Nina Sayers was far from the first role that should have won her the highest award in #Hollywood.
Given the choices between Closer and Garden State, it's hard to choose which role was more deserving of an Oscar. (I would have given her awards for both!) Although Portman was nominated for Best Supporting Actress for Closer, her role as Samantha in Garden State unfortunately flew under the radar. With both of these roles, she showed that her ability to connect emotionally with the character in front of her is unparalleled.
I have no doubt that Black Swan won't be Portman's only Oscar, but it by no means should have been her first.
Who is your favorite Oscar-winning actor? Who deserves an Oscar but doesn't have one yet? Let us know in the comments!