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Award Season Victors: 15 of the Most Successful Oscar Winners in the Past and Five Bad Ones

Updated on November 27, 2019
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Heather has a Bachelor's Degree in English from Moravian College and has been freelance writing for more than 14 years.

Is it just an honor to be nominated? Sometimes, but many nominees preferred the idea of winning over all others. When your name gets called, it confirms every sense of achievement you have been planning since you were little. The question next remains is, now what? What do you do to top this win?

Since 1929, the Academy Awards has been giving awards to the best of the best. The cream of the crop. Well, sometimes the awards are given to the right people, but there are a few times where viewers were puzzled when an unexpected name was called. Not like when presenters Warren Beatty and Faye Dunaway called the wrong winner for Best Picture. Take for instance when Marisa Tomei won for Best Supporting Actress for My Cousin Vinny. It seemed like such light fare when they were plenty of other more deserving winners in that category that year. She has proven herself in subsequent years, but it was a head scratcher at the time.

Sure, you can start to notice when the Academy tended to favor over a certain actor or actress above all others based on the number of times they were nominated and the times they've won. Here is a list of 15 Oscars winner that have won multiple times or made a lasting impression. There is also a list five past winners who have not properly followed up their Oscar victories. Read on to see if your favorite performer made the cut.

As Good As It Gets Poster
As Good As It Gets Poster
Lincoln Poster
Lincoln Poster
Training Day Poster
Training Day Poster
Rain Man Poster
Rain Man Poster
Million Dollar Baby Poster
Million Dollar Baby Poster
Raging Bull Poster
Raging Bull Poster

Best Actor/Director Victories

Jack Nicholson- As an actor, Jack Nicholson had a strong screen presence that made him equal parts fascinating and terrifying to watch. Audiences couldn't help to want to root for him, even when he was playing the villain. Nicholson has three Oscar wins to his credit in three separate decades, which showcased his enduring staying power in movies. His first Oscar came for 1975's One Flew Over the Cuckoo's Nest where he won Best Actor. His second Oscar came with 1983's Terms of Endearment as a Best Supporting Actor. His last Oscar win came as Best Actor for 1997's As Good As It Gets. Over the course of his acting career, Nicholson has garnered 12 nominations as a whole. In recent years, his career has seemed to slow down, but never say never to another nomination or win.

Denzel Washington- As an actor, Washington was able to elevate even the most lackluster of material. It was rumored that he was in talks to play a new version of Magneto now that X-Men is part of the Marvel banner. His first win came with 1989's Glory as a Best Supporting Actor as a slave who fought in the Union Army. He showed a strong presence and strength even when his character was being whipped. His second win came for Best Actor for 2001's Training Day, which made him only the second African American to win a Best Actor Oscar since Sidney Poitier did for 1963's Lilies of the Field. Washington's performance made what could've been a one note character in someone else's shoes a magnetic watch from start to finish. Even though he was the villain, audiences couldn't take their eyes off him whenever he was on the screen.

Daniel Day-Lewis- The notorious method actor has won three Oscars through the course of his career. He was nominated a total of six times and has supposedly retired from acting after 2017's Phantom Thread. He won all three of his Oscars in the Best Actor category for 1989's My Left Foot, 2007's There Will Be Blood and 2012's Lincoln. Day-Lewis was handsomely rewarded by the Academy for his intense efforts to literally become the character. Understandable that he wanted to retire because method acting like that can take a toll on your true identity. It's a shame, but hopefully he will return to Hollywood in some capacity. Doubtful, but one can hope.

Robert De Niro- The legendary actor has won twice for 1974's The Godfather Part II as Best Supporting Actor as a younger Vito Corleone. He won a Best Actor Oscar for 1980's Raging Bull as real life boxer Jake LaMotta. He has been nominated a total seven times, but he still managed to draw people in his varying performances in different film genres. Some were successful, while others were wisely overlooked.

Dustin Hoffman- Since his breakthrough role in The Graduate, Hoffman has been nominated a total of seven times and won twice for his roles in Kramer Vs. Kramer (1979) and Rain Man (1988). Each win was for the Best Actor category and each performance showcased two different characters with very differing levels of vulnerability. One was going through a painful divorce and raising his son alone. The other involved a gifted savant who loved his younger brother, but was unable to connect with him due to his medical condition. Hoffman continued to work, but his reputation of being difficult to work with in the past sometimes made it a challenge to find the right project for him.

Clint Eastwood- This actor/director was a multi talented threat in Hollywood who had been directing his own movies for years by 1992's Unforgiven. That film was a western by a former killer doing one last job as an act of redemption. That was Eastwood's first win for Best Director. With 2004's Million Dollar Baby, Eastwood garnered his second win in that category. His films where he was behind the camera focused on capturing human emotion, even when it was people at their lowest points and also their highest ones as well.

The Good Earth Poster
The Good Earth Poster
Forrest Gump Poster
Forrest Gump Poster
Julia Poster
Julia Poster

Back to Back Winners

Luise Rainer - In Hollywood's early days, some stars could win the big awards early in their careers. That was the case of Rainer who won back to back Best Actress Oscars for 1936's The Great Ziegfeld and 1937's The Good Earth. In both films, Rainer demonstrated talent that many actresses dreamed about showcasing. She was able to do it so early in her career that she was never really able to sustain it sadly.

Tom Hanks- Since his career took in the 1980s, Hanks has demonstrated through his talent and likable personality that he could play almost anything. He's rarely had a box office bomb and he went through the ringer in the 1990s to play his award winner performances. In 1993's Philadelphia, he played a lawyer dying of AIDS who sued his former law firm for discrimination. He brought a face to a very brutal illness as he physically withered on the screen. In 1994's Forrest Gump, he played a man with simple desires that ended up capturing the hearts of the audience. Sure, the movie was syrupy at times, but Hanks made it convincing syrup all the same.

Jason Robards- In the 1970s, Robards brought a certain level of authority to his films. He might not have had a lot of screen time, but he made his presence known however long he was there. He won two back to back Oscars as Best Supporting Actor for 1976's All the President's Men and 1977's Julia as Dashiell Hammett. Robards earned a total of 3 nominations in his lifetime and won for most of them, which demonstrated a lot of power in only supporting roles.

Clift and de Havilland shared a scene together in The Heiress.
Clift and de Havilland shared a scene together in The Heiress.
On Golden Pond Poster
On Golden Pond Poster
The Iron Lady Poster
The Iron Lady Poster
Butterfield 8 Poster
Butterfield 8 Poster
Coming Home Poster
Coming Home Poster
The Silence of the Lambs Poster
The Silence of the Lambs Poster

Top Tier Actresses

Olivia de Havilland- Through the course of her career, Olivia de Havilland has brought a level of class and dignity as she played characters going through varying degrees of difficulty. She was nominated five times for Oscars in her career and won twice for Best Actress in 1946's To Each His Own and 1949's The Heiress by playing women who were stronger than their circumstances. She brought a level of dignity and a subtle nature even when playing the villain in Hush…Hush, Sweet Charlotte. The still living de Havilland was the embodiment of a now bygone era, unless you had on Turner Classic Movies to relive those days.

Katharine Hepburn- The Academy Award Winning actress was nominated 12 times in the course of her lifetime and won four of those times as Best Actress in various points of her career. Her first win came for 1933's Morning Glory. The other three came in the later days of her acting career with 1967's Guess Who's Coming to Dinner, 1968's The Lion in Winter and 1981's On Golden Pond. Hepburn had the most nominations in Academy history, until the next person on the list bested her record.

Meryl Streep- When it comes to nominations, Streep has the most of any actor, living or otherwise, with 21 nominations. It seems she is the belle at the Academy Awards ball by simply having to read the phone book and a get a nomination. She has won three times with 1979's Kramer Vs. Kramer as Best Supporting Actress as a mother fighting for custody of her son in a bitter divorce. For her two Best Actress wins, she won for 1982's heartbreaking Sophie's Choice about a woman forced to make a terrible choice and for 2011's The Iron Lady as Margaret Thatcher. She played the controversial British Prime Minister with a level of gusto and passion that the rest of the film sorely lacked. Streep was the reason to see that movie and she deserved her third Oscar win for it.

Elizabeth Taylor- Taylor grew up as a child in the studio system and evolved into a vulnerably glamorous talent. She garnered awards and tabloid controversy for her many marriages and affairs. Her first Best Actress win came for 1960's Butterfield 8, which was rumored to be out of sympathy due to a major illness she was going through around that time. For 1966's Who's Afraid of Virginia Woolf?, there was no doubt that she deserved the recognition for playing one half of a voraciously bitter married couple. She tore into every one of her scenes with vigor and deserved the awards for doing so.

Jodie Foster- This actress/director has been in the industry since she was a child and grew up into an award winning actress. She has been nominated four times and won twice for her work as Best Actress in 1988's The Accused as a rape survivor and as Clarice Starling in 1991's The Silence of the Lambs. In recent years, Foster has scaled back her work input, but when she does choose to work she puts the right amount of intensity into each project either in front of or behind the camera.

Jane Fonda- Fonda grew up in an acting dynasty, but has created a legacy all her own through her work and off-screen activism. She has been nominated a total of 7 times in her career and won twice in the Best Actress category for 1971's Klute and 1978's Coming Home. She continues to work in movies and on her television show Grace & Frankie. Fonda shows no signs of slowing down anytime soon.

Braveheart Poster
Braveheart Poster
Monster's Ball Poster
Monster's Ball Poster
Leaving Las Vegas Poster
Leaving Las Vegas Poster
L.A. Confidential Poster
L.A. Confidential Poster
Ray Poster
Ray Poster

Failed to Follow-Up

Nicolas Cage- Sadly, after winning Best Actor for 1995's Leaving Las Vegas, Cage shifted his efforts into being a successful action star at the box office. He figured that he got all the accolades and that he wanted to make enough money now. Unfortunately, a string of failed films critically and commercially have caused him to lose his box office luster. He also burned through all of his money through poor spending habits. Maybe, he will one day be back in his former glory days, but that won't be happening anytime soon.

Jamie Foxx- After winning Best Actor for 2004's Ray, Foxx also chose to go the same commercial route that Cage took. The results have been mixed at best. He also took a foray into a music career and a hosting gig on Fox's Beat Shazam. Maybe one day, Foxx will reclaim his box office crown, but he needs to choose his film projects more wisely to do so.

Halle Berry- One word: Catwoman. It was Berry's biggest mistake to follow up the success of 2001's Monster's Ball and her win as Best Actress for it with this 2004 albatross of a movie. The film was bad from start to finish and earned her a Razzie award for her efforts. Her career has never been the same since.

Mel Gibson- For decades, the actor/director was at the top of the Hollywood hierarchy, but it was a string of bad behavior and voice mails in the 2000s that led him to be persona non grata. The Oscar winner won Best Director for his work in 1995's Braveheart. He's slowly managed to regain some of his former glory, but he still has a long way to go.

Kim Basinger- Poor film choices led this Best Supporting Actress winner for 1997's L.A. Confidential and a painful tabloid heavy divorce from Alec Baldwin into filmmaking obscurity. She could no longer be cast as the ingenue or the femme fatale, but maybe one day the right role will come along again to prove the Academy right.

In the end, the Academy Awards will continue to award deserving winners and offer at least a few curveballs each year to keep viewers guessing. There is always at least one or two categories of the big five that are complete wild cards where everyone could have a chance to win. Controversies can erupt when you least expect it from too much favoritism or lacking racial diversity like it did one year. That will never change because not everyone can be satisfied when it comes to awards season. It's just not possible to please everyone.

Meryl Streep will likely earn more nominations because she was an Academy darling and a critically acclaimed movie darling will win Best Picture to the surprise of many. The Oscars loved their musicals no matter how many cynics were members. Nowadays, there was a conflict between franchise flicks and arthouse fare, but with the holiday season approaching the latter will likely be the belle of the Oscar's ball come next year. Only time will tell if that's the case, but it's likely a certainty that next year will be no different.

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