Richest Oscar-Winning Actors in Hollywood

Meryl Streep
"The Laundromat" North American Premiere | Emma McIntyre/Getty Images

The bright lights of Hollywood represent the possibility of fame and fortune beyond most people’s wildest dreams. In reality, the great majority of actors and actresses who take the leap into the film industry world find much more rejection and frustration than success.

However, the fans don’t notice the failures, only the stars. A select few have managed to build careers that combine commercial success at the box office and artistic success with the critics. Below is a list of actors and actresses who have won Academy Awards and managed their finances well enough to build fortunes estimated at over $100 million.

1. George Clooney

George Clooney
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Oscars: Best Supporting Actor, Syriana and Best Picture, Argo

Net Worth: $500 million

George Clooney first built his star power on the small screen, as the leading hunk Doug Ross on the television series ER from 1994-1999. This role earned him high-profile leading roles on the big screen in the romantic comedy One Fine Day (1996) and as Batman in Batman & Robin (1997). It wasn’t until the release of Syriana in 2005 that Clooney fully earned his acting chops in his Oscar-winning performance as world-weary CIA agent Bob Barnes.

Along with his Oscar for acting, Clooney also took home a gold statue as producer of Argo, which won Best Picture of the Year in 2012. Clooney is not just a pretty face, but is also proficient on the other side of the camera. Clooney has earned three nominations for Best Actor, two nominations for Best Screenplay, and another for Best Director.

While acting has paid the bills, Clooney has raked a good bit of dough as a long-time spokesman for Nespresso. A great portion of his estimated $500 million fortune came in 2017 when he and his business partner Rande Gerber sold their Casamigos tequila for $1 billion.

2. Robert De Niro

Robert De Niro
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Oscars: Best Actor, Raging Bull and Best Supporting Actor, The Godfather: Part II

Net Worth: $500 million

Robert De Niro was still virtually unknown when he played the young version of Vito Corleone in Francis Ford Coppola’s classic, The Godfather: Part II in 1974. De Niro went on to prove that the Best Supporting Actor award he won that year was no fluke; he followed up with Best Actor nominations for his performances in Taxi Driver (1976) and The Deer Hunter (1978). De Niro won his second Oscar for his portrayal of boxer Jake La Motta in Martin Scorcese’s film Raging Bull in 1980. Since then, De Niro earned three more Oscar nominations but has fallen short of his third golden statue.

In addition to his prolific on-screen success, De Niro has broad commercial ventures. While recent estimates put De Niro’s fortune at half-a-billion dollars, it’s unclear how much his 2018 divorce and the 2020 COVID-19 pandemic have affected his bottom line.

3. Jack Nicholson

Jack Nicholson
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Oscars: Best Actor, One Flew Over the Cuckoo’s Nest, Terms of Endearment, As Good as It Gets

Net Worth: $400 million

While he might not be the richest actor in Hollywood, very few can approach his record of success with the Academy of Motion Picture Arts and Sciences. Over five decades, Nicholson has earned a total of twelve Oscar nominations, from his first Best Supporting Actor nomination in the ‘60’s classic Easy Rider (1969) to his deadpan portrayal of middle-aged angst in About Schmidt (2002). His Academy Awards came from unforgettable roles as the rebel McMurphy in One Flew Over the Cuckoo’s Nest (1975), a retired astronaut with a Peter Pan complex in Terms of Endearment (1983), and the gruff, reclusive author who finds love in As Good as It Gets (1997).

While the die-hard Lakers fan has perfected a happy-go-lucky persona on-screen and off, Nicholson has carefully built and maintained a vast fortune through shrewd negotiations that guarantee him a percentage of the box office proceeds as well as a top-notch salary for his incredible skills.

4. Sylvester Stallone

Sylvester Stallone
Premiere Of "One Night: Joshua Vs. Ruiz" | Leon Bennett/Getty Images

Oscar: Best Picture, Rocky

Net Worth: $400 million

Allright, so while technically Stallone has never won an Academy Award for his acting, Rocky earned him nominations for Best Actor and Best Original Screenplay and went on to win Best Picture of 1976 and become a smash hit at the box office. Stallone earned a second Oscar nomination for Best Supporting Actor for his performance in the same role as Rocky Balboa in Creed (2015), almost 40 years after his first nomination.

Stallone has built an immense fortune over the last four decades by sticking with his winning formula of heroes fighting corrupt powers and winning against all odds. In addition to the Rocky franchise, Stallone has created and produced global blockbusters built around a persecuted Vietnam vet in the Rambo series, an indefatigable mercenary Barney Ross in the Expendables movies, and as prison expert Ray Breslin in the Escape Plan franchise.

5. Tom Hanks

Tom Hanks
92nd Annual Academy Awards - Arrivals | Kevin Mazur/Getty Images

Oscars: Best Actor, Philadelphia and Forrest Gump

Net Worth: $400 million

Tom Hanks is quite possibly the best-loved actor in Hollywood, due to his incomparable combination of acting skills and humble generosity. Unlike most stars, Hanks seems to effortlessly shine on the screen, as well as being able to relate to fans and co-stars of all backgrounds on set. Along with supplying the voice for Woody in Disney’s Toy Story franchise, Hanks has earned a total of six Oscar nominations over a 31-year period, from Big (1988) to A Beautiful Day in the Neighborhood (2019). But the mid-1990s belonged to Hanks alone, due to back-to-back Best Actor Oscar wins for his portrayal of an attorney battling AIDS and bigotry in Philadelphia (1993) and the one-of-a-kind friend to all in the classic Forrest Gump (1994).

Hanks has a well-earned reputation for his generous support of a range of causes and organizations. He and wife Rita Wilson, whom he met on the set of the TV comedy Bosom Buddies, have built a very hefty fortune around his A-list salary and a series of savvy investments.

6. Cher

Cher
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Oscar: Best Actress, Moonstruck

Net Worth: $360 million

If it seems like Cher has been around forever, it might be because her career has lasted longer than virtually any other in the entertainment industry. As a teenager, Cher was already singing backup vocals on Phil Spector-produced pop hits like “You Lost That Lovin’ Feelin’” and “Be My Baby” before marrying singer Sonny Bono. A pop star in the ‘60s and ‘70s, Cher shifted her talents to the big screen in the ‘80s, with solid performances in Silkwood (1983), Mask (1985) and The Witches of Eastwick (1987) before striking Oscar gold in Moonstruck (1987) as widow Loretta Castorini, a woman torn between romance and family obligations.

While fans and critics alike have been drawn to Cher’s film performances, most recently a show-stopping cameo in Mamma Mia! Here We Go Again (2018), Cher’s vast fortune has come mainly from her draw as a musical performer. Cher has untold millions pouring in from a combination of record sales, lucrative tours, and a multi-year residence at Caesars Palace in Las Vegas.

7. Michael Douglas

Michael Douglas
26th Annual Screen Actors Guild Awards - Arrivals | Leon Bennett/Getty Images

Oscars: Best Actor, Wall Street and Producer, One Flew Over the Cuckoo’s Nest

Net Worth: $350 million

Michael Douglas followed in his father Kirk Douglas’ footsteps in forging a long and successful career as an actor in both film and television. His first high profile role was in the hit TV crime series The Streets of San Francisco. However, his first experience with Oscar gold came as a producer for the adaptation of the Ken Kesey novel, One Flew Over the Cuckoo’s Nest, after buying the screen rights from his dad. An instant classic, the film ran the big categories at the Academy Awards, including Best Picture, Best Director, Best Screenplay, Best Actor, and Best Actress and raked in some $180 million at the box office. Twelve years later, Douglas took home an Oscar for his work as the win-at-all-costs uber-capitalist Gordon Gecko in Oliver Stone’s Wall Street (1987).

After four decades at the top of his game on both sides of the camera, Douglas has built a tremendous fortune to accompany his storied career. Michael’s father Kirk did not include his son in his will before passing away in Feb. 2020, choosing instead to donate his entire estate to various charities. Only time will tell if Michael will follow his father’s lead once again.

8. Sean Connery

Dennis Keogh
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Oscar: Best Supporting Actor, The Untouchables

Net Worth: $350 million

As the first actor to portray Ian Fleming’s James Bond, Sean Connery brought an alluring blend of physical prowess and suave indifference to the character. Somewhat a victim of his own success as 007 in six classic films, Connery appeared in a series of roles throughout the 70’s and 80’s that failed to set the screen on fire, including the utterly forgettable Never Say Never Again (1983), a corny remake of Thunderball (1965). But when director Brian De Palma needed to cast a streetwise, no-bullshit Irish cop for his Prohibition-era masterpiece The Untouchables (1987), Connery filled the role perfectly, earning the Oscar for Best Supporting Actor in the process.

Before achieving success on the silver screen, Scottish-born Connery held a series of blue-collar jobs, before taking the stage as a competitive bodybuilder. His strong work ethic and relatively humble lifestyle have combined to nurture a fortune beyond the dreams of the evil supervillains from the early-60’s Bond films.

9. Brad Pitt

Brad Pitt
92nd Annual Academy Awards - Press Room | Albert L. Ortega/Getty Images

Oscars: Best Supporting Actor, Once Upon a Time in Hollywood and Producer, 12 Years a Slave

Net Worth: $300 million

Proving that perseverance pays off, Pitt won an Oscar twenty-four years after the first of his four nominations. After a part in Thelma and Louise (1991) thrust him into instant star status, Pitt worked hard to find meaningful roles to show he was more than just a pretty face (and a perfect body). Strong performances in A River Runs Through It (1992) and Legends of the Fall (1994) primed critics to take notice of his acting skills, so by the time he joined the cast of Terry Gilliam’s sci-fi dystopian fantasy 12 Monkeys (1995), Pitt was able to join the elite with his first Oscar nomination as Best Supporting Actor. Eighteen years later, Pitt grabbed his first golden statue as one of the co-producers of 2013 Best Picture 12 Years a Slave and returned six years later to grab his first Academy Award as an actor, for his supporting role as trippy stuntman in Quentin Tarantino’s Once Upon a Time in Hollywood (2019).

For whatever success Pitt has enjoyed as an actor and producer (Moneyball (2011) and The Big Short (2015) also earned Best Picture nominations), fans have been most keenly interested in his celebrity lifestyle, including his two high-profile marriages -- and divorces -- with actresses Jennifer Aniston and Angelina Jolie.

10. Leonardo DiCaprio

Leonardo DiCaprio
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Oscar: Best Actor, The Revenant

Net Worth: $260 million

A professional television actor since the age of 5, DiCaprio was a movie star as a teenager due to solid performances in What’s Eating Gilbert Grape (1993) and The Basketball Diaries (1995). However, it was James Cameron’s Titanic (1997) that thrust Leo into superstardom and gave him almost unlimited freedom to choose the most coveted roles in Hollywood. After coming up short in four Oscar nominations over a period of twenty years, Leo finally won an Oscar in 2016 for his performance as Hugh Glass, a frozen frontiersman overcoming all odds in The Revenant. This past year, DiCaprio earned his sixth Academy Award nomination but lost out to Joaquin Phoenix for his disturbing performance in The Joker.

In addition to his unparalleled run in commercial and artistic successes, DiCaprio has fully leaned into the off-screen role of Hollywood superstar, including a series of relationships with many of the world’s top supermodels, sun-splashed Mediterranean holidays on mega-yachts, private jets, and his own private island in the Caribbean.

11. Denzel Washington

Denzel Washington
47th AFI Life Achievement Award Honoring Denzel Washington - Inside | Kevin Winter/Getty Images

Oscar: Best Actor, Training Day + Best Supporting Actor, Glory

Net Worth: $250 million

Over the last thirty years, Denzel Washington has continually captivated audiences, earning eight Academy Award nominations that yielded wins in both the Best Supporting and Best Actor categories. Washington earned his first Oscar nomination for his portrayal of a crusading South African journalist targeted by the apartheid regime in Cry Freedom (1987) and took home a statue two years later for his supporting role as a heroic Union soldier in the Civil War epic Glory (1989). His win helped propel him into leading roles, including a breakout performance as the legendary civil rights leader in Malcom X (1992) and additional heroic roles in The Pelican Brief (1993), Philadelphia (1993), Crimson Tide (1995), The Hurricane (1999), and Remember the Titans (2000). But it wasn’t until Denzel played the bad guy Alonzo in Training Day (2001) that the Academy acknowledged his talents with an Oscar for Best Actor.

Denzel’s talents have put him in the elite level of actors. He has been able to command eight-figure salaries for multiple roles over the last several decades and he credits his decision to abstain from drinking and drugs to amassing a fortune well into nine figures. Unlike many of his Hollywood colleagues, Denzel has managed to preserve a high degree of privacy and has written several million-dollar checks to his favorite religious and educational charities.

12. Julia Roberts

Julia Roberts
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Oscar: Best Actress, Erin Brockovich

Net Worth: $250 million

Julia Roberts had a great deal of success at the very earliest stages of her film career. After standing out as independent small town waitress Daisy in the sleeper hit Mystic Pizza (1988), and receiving two Oscar nominations for her performances in Steel Magnolias (1989) and Pretty Woman (1990),  Roberts was firmly entrenched in the movie star scene. After a mixed run of hits and flops in the 1990s, Roberts started the new millennium strong with an unforgettable performance as the take-no-prisoners legal aide fighting for justice in Erin Brockovich (2000).

As a top leading lady, Roberts has continually earned salaries of +$20 million-per-movie, due in part to a world-champion smile that reportedly has been insured for $30 million. Her consistent box office success had provided the means for Roberts to indulge in her love of horses with a sprawling ranch and stables in Malibu while leaving plenty left over in the bank account for generations to come.

13. Morgan Freeman

Morgan Freeman
American Black Film Festival Honors Awards Ceremony - Backstage | Amy Sussman/Getty Images

Oscar: Best Supporting Actor, Million Dollar Baby

Net Worth: $250 million

While there are plenty of stories of actors and actresses peaking too early, Morgan Freeman proves it’s never too late to grab the brass ring. After a few acting parts in the 60’s, Freeman’s acting career finally started paying the bills after he joined the cast of The Electric Company as Mark/Easy Reader for six seasons. Freeman worked steadily between film and television throughout the 80s, but it wasn’t until Unforgiven (1992), The Shawshank Redemption (1994), and Se7en (1995) that Freeman started earning strong accolades from critics and fans alike. After winning an Best Supporting Actor Oscar in Clint Eastwood’s Million Dollar Baby (2004), Freeman has found no shortage of featured roles in big budget movies, including the sage Fox in The Dark Knight series, as Nelson Mandela in Invictus (2010), and as Allan Trumbull in Olympus Has Fallen (2013) and its two sequels.

Unlike the strong trend to feature the hottest, youngest, most attractive actors available, Freeman has proven himself a valuable commodity playing the wise old man, cashing in on many, many millions in the process.

14. Nicole Kidman

Nicole Kidman
26th Annual Screen Actors Guild Awards - Arrivals | Leon Bennett/Getty Images

Oscar: Best Actress, The Hours

Net Worth: $250 million

Born in Hawaii but raised in Australia, Kidman built her career with roles on Australian television series, and with roles such as Dr. Claire Lewicki in Days of Thunder (1990), Dr. Chase Meridian in Batman Forever (1995), and Dr. Julia Kelly in The Peacemaker (1997). Kidman’s career shifted dramatically at the end of the 90’s, co-starring with her then-husband Tom Cruise in Stanley Kubrick’s psycho-erotic thriller Eyes Wide Shut (1999) and then as the vivacious Satine in Moulin Rouge (2001), a film which earned her the first of four Oscar nominations. Her sole Academy Award win came the following year, in recognition of her portrayal of poet Virginia Woolf in The Hours

After her divorce from Cruise was finalized in 2001, Kidman was a prodigious worker, often appearing in several releases per calendar year over the following decade. A combination of her divorce settlement, steady and large paychecks, a number of lucrative advertising campaigns, and her 2006 marriage to country recording star Keith Urban have helped Kidman grow her fortune beyond what anyone could have expected when she was a teenager on Australian TV.

15. Reese Witherspoon

Reese Witherspoon
2020 Vanity Fair Oscar Party Hosted By Radhika Jones - Arrivals | Karwai Tang/Getty Images

Oscar: Best Actress, Walk the Line

Net Worth: $200 million

Though Witherspoon’s most iconic role was as the smarter-than-she-seems Elle Woods in Legally Blonde (2001), Reese won the Academy Award for Best Actress for her performance in Walk the Line (2005) as the resolute June Carter Cash alongside Joaquin Phoenix as Johnny Cash. While subsequent roles in Wild (2014) and the TV miniseries Big Little Lies earned additional award nominations, Witherspoon’s film career has been uneven over the past decade or so, including some large budget romantic comedies like How Do You Know (2010) and This Means War (2012) that failed with fans and critics alike.

Aside from the millions she has earned as an actor, Witherspoon has secured additional revenue streams by tapping into her entrepreneurial vision and skills, including the 2012 launch of her own production company Pacific Standard (now part of her production company Hello Sunshine) and the 2015 launch of her own fashion line Draper James, named in honor of her grandparents.

16. Sandra Bullock

Sandra Bullock
77th Annual Golden Globe Awards - Press Room | Kevin Winter/Getty Images

Oscar:  Best Actress, The Blind Side

Net Worth: $200 million

Bullock sustained a steady stream of movie parts throughout the 90’s and 00’s in a series of romantic comedies such as Miss Congeniality (2000) and light action vehicles such as Speed (1994), which didn’t call on Bullock to deliver much dramatic depth. In 2009, however, Bullock’s performance as the tough-love mama bear ex-cheerleader Leigh Anne Toughy in The Blind Side made critics stand up and take notice, resulting in her first Oscar nomination and a win for Best Actress.

Bullock’s artistic and commercial success in The Blind Side set her up to negotiate a terrific package for Gravity (2013), in which she reportedly raked in some $70 million between an eight-figure salary and a guaranteed percentage of the box office gross.

17. Matt Damon

Matt Damon
Matt Damon Visits The SiriusXM Hollywood Studios in Los Angeles | Emma McIntyre/Getty Images

Oscar: Best Screenplay, Good Will Hunting

Net Worth: $170 million

While perhaps he doesn’t fit 100% with the rest of the list, Damon is technically an Oscar-winning actor, even though his one Oscar was not awarded for acting. Damon shared his only Oscar to date for the screenplay for Good Will Hunting (1997), which he co-wrote together with childhood friend Ben Affleck. Damon picked up additional Academy Award nominations for Invictus (2009) and The Martian (2015).

Not just a pretty face, Damon nearly completed his bachelor’s degree at Harvard before dropping out to pursue his Hollywood career, a decision that has paid off handsomely with high-budget roles in the Ocean’s trilogy and as Jason Bourne in four blockbuster releases to date. In between starring roles, Damon commands top dollar for commercials, reportedly pocketing a cool $3 million for a single Nespresso commercial back in 2013.

18. Al Pacino

Al Pacino
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Oscar:  Best Actor, Scent of a Woman

Net Worth: $165 million

Al Pacino earned his first Academy Award nomination for his iconic role as Michael Corleone in The Godfather (1972), but his first win came two decades later as the hard-as-nails Lt. Col. Frank Slade in Scent of A Woman (1992). In between, Pacino  earned an additional six Oscar nominations in addition to playing Tony Montana in Scarface (1983).

Although decades of quality performances in artistic and box office hits have swelled Pacino’s investment portfolio, his fans might be surprised by some of the huge roles he passed on, including Han Solo in Star Wars (1977) and Axel Foley in Beverly Hills Cop (1984).

19. Angelina Jolie

Angelina Jolie
"Maleficent: Mistress Of Evil" European Premiere - Red Carpet Arrivals | Jeff Spicer/Getty Images

Oscar:  Best Supporting Actress, Girl, Interrupted

Net Worth: $160 million

Long before she and Brad Pitt became the hottest couple in Hollywood after sparking a romance on the set of Mr. & Mrs. Smith (2005), Angelina Jolie nabbed an Oscar for Best Supporting Actress in the psychological drama Girl, Interrupted (1999). Following on her Oscar, Jolie racked up a long list of uneven releases that were often far more popular with the fans than the critics, leading Jolie to become the highest-paid female movie star by the end of the 2000’s. 

Over the last decade, Jolie has been featured in blockbuster hits like Maleficent (2014) and Maleficent: Mistress of Evil (2019), which together raked in over $1.2 billion worldwide. This success gave her the artistic freedom to pursue a range of humanitarian projects as well as directing. On her approach to money, Jolie laid out an obviously successful formula for her: “Save one-third, live on one-third, and give away one-third.”

20. Anthony Hopkins

Anthony Hopkins
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Oscar: Best Actor, Silence of the Lambs

Net Worth: $160 million

Welsh-born Anthony Hopkins turned in a historic performance in Jonathan Demme’s psycho-thriller The Silence of the Lambs (1991), for which he won an Oscar for Best Actor. Since then, Hopkins has earned an additional four Academy Award nominations.

Off set, Hopkins has steered clear of the drama and turmoil of stardom, preferring instead to work on his craft and quietly deposit the salaries that recognize him as one of the great artists working in Hollywood today. Before becoming a U.S. citizen in 2000, Hopkins was appointed Commander of the Most Excellent Order of the British Empire by Queen Elizabeth II.

21. Charlize Theron

Charlize Theron
92nd Annual Academy Awards - Arrivals | Jeff Kravitz/Getty Images

Oscar:  Best Actress, Monster

Net Worth: $160 million

Born and raised in South Africa, Theron overcame a series of childhood hardships, including an abusive father who was ultimately shot and killed by her mother. Already working as a professional model by 16, Theron trained hard as a ballet dancer before her knees gave out, forcing her to try acting as a fallback plan. After a few lucky breaks, and a series of commercial hits, Theron won the recognition of the Academy for her performance in Monster (2003).

On set, Theron throws caution to the wind in order to perform her own stunts, resulting in a few close calls, including a herniated disc in her neck while filming Aeon Flux (2005). Already one of the highest paid actresses in Hollywood, Theron’s timeless beauty has led to lucrative advertising campaigns, including Galliano, Christian Dior, Raymond Weil watches, and Breitling.

22. Meryl Streep

Meryl Streep
2019 Toronto International Film Festival TIFF Tribute Gala - Inside | Matt Winkelmeyer/Getty Images

Oscar:  Best Actress, Kramer vs. Kramer, Sophie’s Choice, The Iron Lady

Net Worth: $150 million

While other actors have cashed bigger paychecks, no one can top Meryl Streep’s career. Streep earned her first Oscar nomination for her understated performance as a Pennsylvania mining-town girl doing her best to comfort Robert De Niro after returning home from Vietnam in the masterpiece The Deer Hunter (1978). Streep’s first gold statue came the following year for her role in Kramer vs Kramer (1979), previewing an unparalleled record of an additional two Oscar wins and another seventeen nominations over the next four decades. 

Before anyone could have guessed she would become a Hollywood star, Streep was a cheerleader and homecoming queen in high school before earning a BA at Vassar and an MFA at Yale. And despite being in the spotlight for so many years, Streep has managed to preserve her privacy and steer clear of gossip and scandal.

23. Gwyneth Paltrow

Gwyneth Paltrow
Harper's Bazaar Exhibtion At Musee Des Arts Decoratifs In Paris | Pascal Le Segretain/Getty Images

Oscar: Best Actress, Shakespeare in Love

Net Worth: $150 million

The daughter of a Hollywood producer/director and an award-winning actress, Paltrow knew from a very early age what it took to be successful in Hollywood. In Shakespeare in Love (1998), Paltrow applied all of her valuable knowledge and skills to full use, taking home an Oscar in her only nomination to date. Since then, Paltrow is probably best known to fans as Pepper Potts from Iron Man (2008) and seven subsequent Marvel releases. Not satisfied with merely being an actress, Paltrow has earned a lot of money as an entrepreneur, including her lifestyle brand Goop and a series of cookbooks.

Before marrying Brad Faclhuk in 2018, Paltrow was linked romantically to a number of celebrities, including a 13-year marriage to Coldplay’s lead singer Chris Martin, an engagement to Brad Pitt, and a long-term relationship with Ben Affleck.

24. Jamie Foxx

Jamie Foxx
American Black Film Festival Honors Awards Ceremony - Backstage | Amy Sussman/Getty Images

Oscar: Best Actor, Ray

Net Worth:  $150 million

Jamie Foxx is a man who’s had success in sports, music, and acting. The year 2004 served as a professional highlight, as Foxx was nominated for Oscars in two categories -- for Best Supporting Actor in Collateral and for Best Actor in Ray, which resulted in a win. Perhaps his most iconic role came eight years later as the lead in Quentin Tarantino’s Django Unchained (2012).

After proving himself one of the top high school quarterbacks in Texas, Foxx shifted his attention to music as a singer and piano player before taking up the dramatic arts. Even when he is shooting films, Foxx devotes considerable time and energy to producing music in his private recording studio, with four Grammys to go along with his Oscar. Foxx recently revealed he was instrumental in helping launch the career of Ed Sheeran.

25. Ben Affleck

Ben Affleck
Ben Affleck Visits The SiriusXM Hollywood Studios | Emma McIntyre/Getty Images

Oscar: Best Picture, Argo + Best Screenplay, Good Will Hunting

Net Worth: $150 million

Like boyhood friend Matt Damon, Affleck’s acting hasn’t won him any Oscars, but the Good Will Hunting (1997) screenplay he and Damon wrote nabbed him his first Oscar. Affleck had to wait 15 years for his second Academy Award, when Argo (2013), which he directed and co-produced with George Clooney, won Best Picture.

Off-screen, Affleck has had a topsy-turvy private life, including being named “Sexiest Man Alive” by People magazine in 2002, becoming a champion professional poker player, and more than one trip to rehab. Currently dating the latest Bond Girl, Ana de Armas, Affleck has had a string of celebrity relationships, including Gwyneth Paltrow, Jennifer Lopez, and a thirteen-year marriage to Jennifer Garner that fell apart after reports of Affleck’s affair with their nanny surfaced.

26. Sean Penn

Sean Penn
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Oscar: Best Actor, Mystic River and Milk

Net Worth: $150 million

Sean Penn broke into Hollywood as a stoned surfer in the classic teen comedy Fast Times at Ridgemont High (1982). Unlike the character Jeff Spicoli, Penn has proven himself to be a devoted professional who has launched himself fully into a variety of roles as actor, director, producer, and political activist. After three Academy Award nominations without a win, Penn finally grabbed his first Oscar for Clint Eastwood’s Mystic River (2003) and earned a second five years later in Gus Van Sant’s Milk (2008).

Penn was married to Madonna in the 1980s and Robin Wright in the 1990s. He has been romantically linked to a number of celebs over the years, including Elizabeth McGovern, Susan Sarandon, singer Jewel, and Charlize Theron. Penn got married for the third time earlier this year to Leila George.

27. Jennifer Lawrence

Jennifer Lawrence
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Oscar: Best Actress, Silver Linings Playbook

Net Worth: $130 million

Oscar: Best Actress, Silver Linings Playbook

Net Worth: $130 million

It’s hard to believe that only ten years ago, Jennifer Lawrence was a little-known actress with only a few television and film credits to her name. Then, suddenly, she seemed to be everywhere, with each starring role associated with great success. Lawrence got a lot of attention for her role as Raven/Mystique in X-Men: First Class (2011) before quickly jumping to superstar status as Katniss Everdeen in The Hunger Games. She won an Oscar for her performance as the freewheeling Tiffany in Silver Linings Playbook, and was thrilling as the lead in the horror film House at the End of the Street

The X-Men and Hunger Games franchises were hits, with several billion in combined box office receipts. Meanwhile, her three collaborations with David O. Russell, (Silver Linings, American Hustle (2013), and Joy (2015))  have captivated critics and cemented Lawrence’s reputation as one of the most talented actresses in Hollywood today.