25. Chelsea Handler – $40,000,000

After a brush with the law left her in a dismal situation, Chelsea Handler was ordered to attend mandatory classes with other offenders. When she relayed her story to her fellow classmates, she received so many laughs that she decided to pursue a career in stand-up.

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At first cast in several minor roles on shows like My Wife and Kids and The Bernie Mac Show, Handler garnered a widespread audience as a commentator on E!, eventually landing her very own show. Now a producer and author in addition to being a famous actress and comedian, Chelsea’s net worth is estimated at $40 million.

24. Whoopi Goldberg – $45,000,000

Born Caryn Elaine Johnson in Manhattan, Whoopi Goldberg earned her stage name from the practical joke toy, whoopie cushions. She moved to California in the 1970s, eventually settling in Berkeley. Whoopi worked several odd jobs, including as a waitress, mortuary cosmetician, and bricklayer, while simultaneously acting with a local theater troupe.

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Before taking over as the host of The View from predecessor Rosie O’Donnell, Goldberg was a star on camera. Her breakout in 1985’s The Color Purple earned her an Oscar and Golden Globe nomination for Best Actress; she would win the latter. She also nabbed a Best Supporting Actress Oscar for her role in Ghost. In addition to hosting and acting, she has also written several books, which have contributed to her $45 million net worth.

23. Jimmy Fallon – $45,000,000

Always the class clown in addition to being an excellent student, Jimmy Fallon ended up dropping out of college to pursue a full-time comedy career in Los Angeles. He performed for $7.50 per set around LA, gaining experience for what he always considered to be his dream job: a role on Saturday Night Live.

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In 1998, he got his chance and secured what would become a historic position for him. The show’s main writer, Tina Fey, once remarked that Fallon and Kristen Wiig were the only two actors who auditioned for SNL that could have started on the same night. Fallon’s gig on SNL eventually led him to host The Late Night Show, and then The Tonight Show, as Jay Leno’s replacement. He is still the host today.

22. Andy Cohen – $50,000,000

After graduating from Boston University with a degree in journalism, St. Louis native Andy Cohen moved to Los Angeles to intern with CBS. He worked mainly as a producer at the company for over ten years, before moving to the Bravo channel, where he occasionally co-hosted alongside Kelly Ripa.

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Cohen is currently an executive producer for Bravo’s Real Housewives series, in addition to hosting the network’s, Watch What Happens Live. As if that weren’t enough, Cohen also has his own Sirius radio talk show. He has written three memoirs that have featured on the New York Times’ bestsellers list, all contributing to his $50 million net worth.

21. Stephen Colbert – $60,000,000

Surprisingly uninterested in comedy as a young man growing up in a large family in South Carolina, Stephen Colbert attended Northwestern University, where he performed in several dramatic plays. Shortly after, he joined a local improv group doing shows at the Annoyance Theater in Chicago, and later joined Second City touring company as an understudy to fellow actor, Steve Carell.

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The latter would eventually land him a writing spot for a new Comedy Central series, called Strangers With Candy. He would continue as a writer for the network’s Daily Show, headed by Jon Stewart, and then hosted his own show The Colbert Report. When Colbert ended his contract, he signed on to CBS and became the host of The Tonight Show, succeeding David Letterman and giving his net worth a serious boost.

20. Trevor Noah – $60,000,000

By 2002, an 18-year-old Trevor Noah was already acting in a South African soap opera and hosting his very own nighttime talk show on the radio. That same year, he dropped acting and radio in order to focus solely on his comedy, touring around South Africa to much success and accolades.

Talk show host, Trevor Noah, interviewing Michael Key on The Daily Show
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By 2011, he had moved permanently to the United States, where he soon secured a recurring position on Comedy Central’s The Daily Show With Jon Stewart. Noah would then go on to become the host of the show himself following Stewart’s retirement in 2017. He still hosts the show, and has published several successful books about his unusual life story.

19. Wendy Williams – $60,000,000

Iconic Jersey girl Wendy Williams was a DJ at her alma mater Northeastern University before finding fame and fortune in television. A Radio Hall of Fame inductee, she became known for her on-air interviews of celebrities working at WBLS radio station in New York, which was syndicated in multiple states across the country during her time as host.

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In 2008, both BET and Fox picked-up on Williams’ radio success, hiring her as the host of her own talk show, The Wendy Williams Show, which still airs today. She has dabbled in television, film, and comedy, in addition to becoming a bona fide fashion entrepreneur constantly raising her net worth thanks to her own clothing and jewelry lines.

18. Michael Strahan – $65,000,000

After a fifteen-year career in the NFL that was capped by winning a Super Bowl in 2007, Michael Strahan decided he’d transition into television. While it was perhaps expected that he might become a football commentator with Fox Sports, it surprised a lot of people when he became a co-host on Good Morning America and Live! With Kelly and Michael, for which he has won two Emmy Awards.

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In 2016, ABC awarded Strahan his own show, reviving the classic game show The $100,000 Pyramid, which is set to air through 2020. In addition to the money he made in football and on television, he has also launched a successful men’s fashion line that is available at retailer J. C. Penney.

17. Jon Stewart – $80,000,000

Growing up during the Vietnam War and the Watergate scandal had a profound effect on Jon Stewart’s political outlook and career. A self-described leftist since his high school days, Stewart has become one of the leading figures in liberalism during the modern era. He would eventually rise from doing late night sets at New York’s Comedy Store for almost no money, to having his own show talk show on MTV.

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The Jon Stewart Show earned the attention of talk show legend David Letterman, who helped Stewart secure a more lucrative contract with network Comedy Central. He would eventually host The Daily Show from 1999, until passing the torch to Trevor Noah in 2015, racking up 22 Emmys in the process. Stewart currently fills his time directing, acting, and appearing as a political commentator for multiple media outlets.

16. Bill O’Reilly – $85,000,000

In between earning his undergraduate and master’s degrees, Bill O’Reilly played semi-professional baseball. He went on to earn a master’s in journalism from Boston University while working as a columnist and reporter for several local newspapers. In the ’80s and ’90s, he worked as a correspondent on multiple news shows for CBS and ABC.

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Fox picked up O’Reilly in 1996, debuting The O’Reilly Factor (originally called The O’Reilly Report), which quickly became the most watched news show on television. Despite receiving criticism from across the spectrum, O’Reilly himself has said that he does not identify with any particular political ideology. In addition to being an on-screen news personality, O’Reilly has authored and co-authored several books on politics and history.

15. Conan O’Brien – $85,000,000

In high school alone, Conan O’Brien worked on the school newspaper, earned an award from the National Teachers Association for authoring a creative short story, and eventually graduated valedictorian. He continued his passion for writing at Harvard, where he wrote for the comedic Harvard Lampoon. Upon graduating and moving to Los Angeles, he wrote for SNL, The Simpsons, and HBO, while regularly performing improv around the city.

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In 2010, O’Brien was named as one of Time Magazine’s 100 Most Influential People. After a sixteen-year career that included long stints as host of Late Night and The Tonight Show, he has taken a hiatus from television. Currently, he hosts his own podcast, Conan O’Brien Needs A Friend, and works as a producer and voiceover actor, in addition to making guest appearances at events.

14. Anderson Cooper – $100,000,000

Son of the railroad and business heiress Gloria Vanderbilt, it might come as a surprise to learn that Anderson Cooper’s journalism career began with rather humble beginnings. After graduating from Yale, he found himself in an entry-level position answering phones at ABC. Looking for a way to break into correspondent work, he counterfeited a press badge, travelling to war-torn countries, selling his ground reporting to news outlets in the States.

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He had a career epiphany one day, realizing that he had become desensitized to the violence that surrounded him, and returned home to work briefly as a reality TV host. He would eventually make a news comeback as an anchor for CNN, where he hosted his own program and won multiple Emmy awards. With an immense net worth, he still anchors Anderson Cooper 360° and also works as an author, guest host, and freelance writer.

13. Bill Maher – $100,000,000

Though Bill Maher eventually followed in his father’s footsteps to become a news personality, the younger Maher’s career first began as a comedian, hosting a variety of comedy shows across New York City. Throughout the ’90s and early 2000s, he was the host of his own show, Politically Incorrect, which aired during separate periods on both Comedy Central and ABC.

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In 2003, he became the host of HBO’s Real Time With Bill Maher, which was nominated for several Emmy’s and Writer’s Guild awards. He appears as a political commentator on multiple networks, including CNN, Fox, and MSNBC, and is vocal on a variety of issues spanning US foreign relations, health care reform, and religion. He also has appeared in several roles in film and television, all adding to his tremendous net worth.

12. Kelly Ripa – $120,000,000

Kelly Ripa was a dancer and starred on the daytime soap opera All My Children, before being discovered by Regis Philbin at a casting call for Live! in 2000. Her fiery personality stood out, immediately winning her the job she still holds today. After casting a rotating lineup of co-hosts to star alongside Ripa, Ryan Seacrest won a permanent role, appearing alongside her currently.

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Offscreen, Ripa serves as a spokeswoman for several leading brands, including 7UP, TD Bank, and Tide. She and her husband also run their own production company, which features documentary films, TV shorts, and series. While Ripa has amassed a fortune during her talk show career, perhaps no accolade is more intrinsically valuable than her Guinness World Record. So what’s it for? She’s had 24 banana cream pies thrown at her at once, a record that still stands today.

11. Steve Harvey – $120,000,000

Steve Harvey’s story is one of rags to riches. As a young man he worked countless odd jobs, and was homeless for three years. He slept in his car and showered in hotels and public swimming pools, while eventually attempting to earn a living as a comic.

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He was finally given a break in 1990, when he won a national comedy search contest earning him a job hosting Showtime at the Apollo. This paved his way to becoming one of the most famous comedians in the country. He has hosted various shows, including his namesake talk show, a reprise of Showtime, and the game show Family Feud, which he hosts today. He also has his own production company and clothing line.

10. Larry King – $150,000,000

The son of two immigrants, Larry King rose from humble beginnings, surviving on welfare after the death of his father drove the family into poverty. In order to support his mother, King moved from his native New York to Florida, taking a job as a local radio show host. He was paid $50 per week serving as a DJ, doing a newscast and sportscast in the afternoon and evening.

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Throughout his illustrious career in radio and television, King has interviewed a variety of guests from all walks of life, from Hollywood celebrities and world leaders to UFO conspiracy theorists. He would host his own talk show for decades until health slowed him down in 2012. King still occasionally guest-hosts events, and runs his charitable foundation providing money to cardiac patients who cannot afford their medical procedures.

9. Sharon Osbourne – $220,000,000

Before hosting her own talk show, Sharon Osbourne was involved in a variety of different business ventures. Her father, Don Arden, was the manager for heavy metal pioneers Black Sabbath, and actually kicked lead singer Ozzy Osbourne out of the band. Little did he realize Ozzy would end up marrying his daughter Sharon! She would eventually take over for her father in managing the band, and later, Osbourne’s solo career.

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National audiences got their first introduction to Mrs. Osbourne in the early reality show The Osbournes, which followed the lives of the family. Her bubbly, raucous, and oftentimes hilarious personality won over fans, earning her several roles on television as a judge on America’s Got Talent and eventually her own namesake talk show that aired in the UK and the US, spiking her net worth. She has written three autobiographies and a novel.

8. Ryan Seacrest – $380,000,000

Ryan Seacrest definitely wins for having the busiest schedule of any talk show host. Always attracted to the idea of being a television host, Seacrest won an internship at his local Atlanta radio station while still in high school. His first broadcast was at 16 as a replacement when a DJ called in sick.

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After hosting countless reality TV show’s Seacrest’s biggest break came when he was cast as the host for American Idol, which led to lucrative deals with E! News, NBC, and Los Angeles radio station KIIS FM. He juggles anywhere from five to ten roles at once, while also running his own fashion line and charity, maintaining an astonishing net worth.

7. Jay Leno – $400,000,000

After graduating from Emerson College in Boston, where he majored in speech therapy and started the school comedy club, Jay Leno appeared in several television shows and movies doing comedy. He frequently was a guest on talk shows rather than hosting. All that changed when he became a regular substitute for Johnny Carson on The Tonight Show in 1986, hosting full-time from 1992.

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NBC would keep Leno on as host until 2004 when Conan O’Brien took over. He would make his talk show return when The Jay Leno Show premiered five years later. Leno claims to have not spent a dime of the money he made from his decades-long career as a television host, living instead off the money he earned from his stand-up comedy. These days, he’s collecting cars, showcasing them on Jay Leno’s Garage.

6. David Letterman – $400,000,000

A self-described average student, David Letterman got his start as a radio DJ on his college campus, eventually getting fired for not playing enough classical music. He would go on to establish his own rival station, landing him on local Indianapolis radio stations as a host and weatherman. With the support of friends and fraternity brothers, Letterman headed to Los Angeles to pursue a career in comedy.

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After dozens of roles and guest appearances on television, Letterman’s sarcastic sense of humor caught the attention of scouts from NBC, who awarded him his own morning show. His time slot was eventually moved, and he would go on to host The Late Show until 2014. Letterman surpassed Johnny Carson as the longest-tenured late night host in US history. He still hosts his own Netflix series, and appears as himself in TV and movies.

5. Dr. Phil McGraw – $400,000,000

Dr. Phil earned his bachelor’s degree in psychology from the University of Tulsa, where he was a member of the varsity football team. He would later go on to earn a master’s in experimental psychology and a doctorate in clinical psychology from North Texas University. In 1990, he joined a legal consulting firm, which was later hired by Oprah Winfrey.

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After multiple appearances as a guest on The Oprah Winfrey Show, McGraw had developed his own following. This led to the creation of the daytime talk show, Dr. Phil, where he offered advice to guests and audience members. The show inspired several reality show spin-offs, all contributing to Dr. Phil’s incredible net worth.

4. Judy Sheindlin – $420,000,000

Judge Judy’s no-nonsense attitude in the courtroom is iconic, but fewer people know about Judith Sheindlin’s background — and how she secured one of the highest-paying positions in television. Prior to becoming one of America’s first reality TV stars, Judy Blum graduated from New York University law school. Soon after, she worked as a corporate lawyer for a cosmetics company, leaving to care for her two young children.

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Sheindlin’s two-year hiatus to be a full-time mother inspired her to pursue a career in family law. After being appointed a New York City judge by then-mayor Ed Koch, Sheindlin made a name for herself for not mincing words. After an article was published in the Los Angeles Times, she caught the eye of reality TV show producers. Judge Judy announced her plans to retire after her 2020-2021 series, ending a 25-year run on television.

3. Ellen DeGeneres – $450,000,000

Before a successful career as a stand-up comedian, Ellen DeGeneres worked a variety of odd jobs. By the early 1980s, she was performing stand-up around her native Louisiana, largely drawing on experiences from her day jobs. By 1984, Showtime had named her the funniest comedian in America, and by the ’90s she was starring in film and television, breaking new ground for LGBTQ visibility in media.

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Short-lived sitcom The Ellen Show earned her the eye of NBC producers, who picked her up as a talk show host and debuted The Ellen DeGeneres Show two years later. As of 2020, the show has won 61 Daytime Emmy awards. Aside from her career as one of America’s favorite TV hosts, Ellen does voice acting, is a spokesperson for several companies, and runs her own lifestyle brand, ED.

2. Howard Stern – $650,000,000

Howard Stern wanted to be a radio personality since the age of five. His father, who also worked in radio, set up a microphone, turntable, and tape recorder in the basement of their home so that his young son could record imaginary shows. Stern worked at a variety of stations, at one time making $100 a week and living in a monastery to save money.

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First hired at WWDC radio in Washington D.C., his rise to fame, while simultaneously recreating his own brand of ‘shock radio’, is well-documented in the 1997 movie, Private Parts, in which Stern stars as himself. His move to satellite radio was ahead of its time, largely because it allowed him the freedom to say whatever he wanted without censorship. His five-year, $500 million contract with Sirius made him the highest paid radio host in history.

1. Oprah Winfrey – $3,200,000,000

Born into poverty to a single mother in rural Mississippi, Oprah Winfrey defied all odds, becoming the highest paid talk show host in history. She got her start in high school working for a local radio station in Tennessee, which led to other jobs in Nashville, followed by Baltimore and Chicago. In 1983, within months of taking over the morning show on WLS-TV, it became the highest rated in the state.

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Oprah’s success on Chicago radio led her to television when her ABC-owned station decided to provide her a platform on camera. The Oprah Winfrey Show which debuted in 1986 and ended in 2011, is one of the longest and most successful television shows in history. Early on, Oprah expanded on her name, venturing into film (garnering her an Oscar nomination), authoring several books, creating her own lifestyle brand that features a magazine and television channel.

Sources: Ask.com, celebritynetworth.com