Potential superstars never actually know their big break is about to be their big break. How can you? It's almost impossible to foresee. Which is why it's so important to trust your gut. Something every single person on this list failed to do. As we all know, hindsight is 20/20. Which is just a better way of saying: you don't know you're about to regret something, until you're looking back on it. All 10 of the listees have spent years kicking themselves over a critical err in judgment, and will likely spend the rest of their lives doing so if a better opportunity doesn't come along to make up for the fatal decision. What's worse is they've had to watch someone else with a better judgment call enjoy the benefits of what they foolishly turned down. Honorable mentions go to Will Smith who turned down the role of Neo in the now iconic film The Matrix, John Travolta who turned down the role of Forrest Gump in Forrest Gump, and Hugh Jackman who turned down a Bond role in Casino Royale. Fortunately for all three actors, they've more than managed to make up for the losses, having each accumulated nine figure net worths. Below are 10 of the most regrettable decisions ever made by celebs that forced them to watch millions of dollars slip through their fingers.
9 Hulk Hogan
Former WWE champ Hulk Hogan, thought the idea of a wrestler endorsing a grill was just ridiculous. Which is exactly why he turned it down when he was presented with the opportunity by his agent in 2000. The wrestler instead opted to endorse a meatball maker that was called "Hulkamania Meatball Maker". Former boxer George Foreman didn't think the idea of endorsing a grill was so bad, so he accepted it after much persuasion from his wife. In just a short pace of time, the grill turned out to be a wild success and these days, most people actually recognize George as the "Foreman Grill guy," more so than for his former boxing profession. Today, George Foreman is worth a staggering $250 million thanks to accumulated royalties from the product endorsement, in stark contrast to Hulk Hogan's $8 million net worth. Ouch is an understatement.
8 Shaquille O'Neal
In 1993 Shaquille O'Neal was approached through his agent by Howard Shultz, with an offer to partner up on a coffee company. Shaquille turned the idea over in his mind and decided that it wouldn't work for the simple fact that, "black people don't drink coffee." At the time the basketball legend couldn't have realized that he was turning down the opportunity to cash in on what would become the $57 billion dollar Starbucks empire. The deal, had Shaq accepted it, would have given him a sizable stake in the company, and the stake would today be worth untold millions. The former Laker recently admitted in an interview with Graham Bensinger, that every time he sees a Starbucks location on every corner, in every city, he's reminded of his greatest business regret to date.
7 Emily Browning
Actress Emily Browning was offered the role of Bella Swan in the Twilight series before the now mega star Kristen Stewart, was ever considered for the part. Emily had just wrapped up filming on The Uninvited, and cited exhaustion as her main reason for turning down the role. The timing could not have been worse for Emily who ultimately turned down upwards of $60 million with the poor decision. Today Kristen enjoys an astronomical net worth of $70 million, 90% of which is the result of Twilight's success, in stark contrast to Emily's $5 million net worth. Emily admits that had she been apart of the Twilight franchise, she would ultimately have quit acting due to all of the attention Kristen Stewart and Robert Pattinson received, which Emily insists she never could've handled.
6 Katie Holmes
Before Sarah Michelle Gellar got the lead role in Buffy the Vampire Slayer, it was offered to 17 year old Katie Holmes, who declined in order to finish high school. After graduating, the same casting director would actually cast her in Dawson's Creek, the following year. Sarah herself wasn't interested in the lead role in the first place, and had initially auditioned for the supporting role of Cordelia Chase, but the director could sense he had a star on his hands with Sarah, so she was given the lead. Today Katie is worth a very comfortable $25 million, but the success of Buffy the Vampire Slayer would have added an extra $15 million to her net worth. Actor Ryan Reynolds was also offered a key role in Buffy, but turned it down because he'd just gotten out of high school and didn't want to play a student, as he felt his high school experience was awful.
5 Paul Shaffer
Musician Paul Shaffer was offered the role of George Costanza by his good friend Jerry Seinfeld, back in 1989 for a new sitcom he was producing. Because of his uncanny resemblance to actor Larry David, of whom the role is based, Paul wasn't even required to audition. The part was his to have if he so chose. Paul's reason for turning down the role was he was too busy leading the band on Late Night With David Letterman, which he's done for the past 30 years. Paul, who's accumulated an estimated net worth of $30 million from having composed the opening theme song for Late Night With David Letterman, missed out on an extra $50 million, which is what Jason Alexander is estimated to be worth thanks to Seinfeld's success.
4 Sean Connery
In 2000, Hollywood Veteran Sean Connery was the first choice for the role of Gandolf in The Lord of The Rings trilogy. Thanks to his star power, the actor was offered $10 million per film, plus 15% of the box office residuals for all three films. Instead of jumping at the very sweet deal, Sean declined the offer due to "not being able to understand the script." Over a decade later, The Lord of The Rings trilogy went on to become one of the highest grossing movie franchises of all time. The former Bond star's take away would have worked out to a total of $480 million had he decided to join the cast. The role for Gandolf eventually went to Ian Mckellen, who at the time wasn't offered as sweet a deal as Sean's due to his lack of star power (which today is no longer a problem).
3 Sandra Bernhard
In 1997, Sandra Bernhard was the first to be offered the role of Miranda Hobbes in the iconic television series, Sex & The City. The actress's reasoning for turning it down was due to what she felt was poor pay, and not wanting to work alongside Sarah Jesica Parker. In an interview with Andy Cohen, Sandra reveals that in her opinion, the script for the pilot was a "disaster", and the pay she was offered was nothing in comparison to what she had earned on Roseanne just a few years prior. The part ultimately went to Cynthia Nixon, who over a decade later, is now worth an impressive $60 million thanks to the show's success. Sandra who today is worth $8 million, admits that she would have over looked her grievances and taken the part had she known the show would turn out as big a success as it had.
2 Pamela Anderson
The X-files star Gillian Anderson, revealed that the original casting call for her character Agent Scully called for a "taller, leggier woman with plenty of curves." Pamela Anderson was reportedly 20th Century Fox's first choice for the role, which is surprising in comparison to the cerebral and moody FBI agent that Gillian ultimately portrayed. Pamela was larger than life at the time, due to her Baywatch fame, and Gillian was an unknown actress, which is why producers were initially against casting the obscure Gillian for the part, but the actress nailed her audition and 20th Century Fox came around. As you can imagine, the show would have been quite different if the buxom blonde had been cast as originally hoped. Today Gillian is worth $25 million thanks to The X-files success, in contrast to Pamela's current $5 million net worth.
2. Dana Delany
In 1997, Dana Delany was approached by her good friend, producer Darren Star, with an offer for the lead role in his new project based on a Candace Bushnell novel involving sex and New York City, no audition required. The problem? Dana had recently completed too many sex themed projects and didn't want to get type cast in the genre. So she respectfully declined. The role eventually went to the lesser known Sarah Jesica Parker, and is today recognized as one of the most iconic television characters in TV history, Carrie Bradshaw. Sarah has a net worth of $90 million in stark contrast to Dana's $8 million. Us Sex & The City fans wouldn't trade Sarah Jessica Parker for the world, but it could've been you Dana. It could've been you.
1 Dave Chappelle
In 2002, Dave Chappelle was at the height of his popularity when Comedy Central offered him $50 million for a 3rd season of his comedy sketch program, The Dave Chappelle Show. Instead of accepting the dream offer, the funny man decided to move to Africa on a whim. Dave explained in an interview with James Lipton that his reason for packing up and moving to Africa at the worst possible timing in his career was due in large part to the overwhelming grief of losing his father at the time of the offer, among other disagreements that the comedian had with executives. The 31 year old at the time received a ton of flack from the public for the unthinkable decision to turn down $50 million and was rumored to have literally lost his mind back then, to which Dave asserts, "To say someone is crazy is dismissive, people are not crazy, they are strong people, maybe their environment is a little sick.” Today, Dave is only worth $10 million.