14 Famous People on the Biggest Risks of Their Careers — and How They Paid Off

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Tons of people start out wanting to be professional entertainers, artists, athletes, and all those other things that allow one to, for the most part, do what they love while getting plenty of money and applause. Most don’t make it, as everyone has heard — including those who do eventually make it. We asked 14 such people to describe the times when they ignored naysayers (and sometimes self-doubt) to take a professional risk that paid off, and how they felt after.

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Katey Sagal
“There have been a lot of projects I have been involved in that didn’t look like they were going to go, and then they go. Married With Children was one — nobody believed in a new network, nobody believed in a raunchy television show,” Sagal told us at the premiere of Bleed for This. “At that point I just needed a job, so I was happy they liked me. But I never thought it would be successful, it just seemed too out of the box for what was going on at the time. So, I think all of us at that time felt a little bit victorious, a little bit of a chuckle of, ‘See we showed you.’”

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Matthew Morrison
“I think just moving to New York City right out of high school,” said the actor at a screening of Allied hosted by the Cinema Society and Chandon. “I grew up in Southern California and sometimes I look back and I’m in awe of my 18-year-old self to have the courage to come out here and try to make it [in theater]. I think that was the riskiest thing I’ve ever done.”

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Judd Apatow
“I think every movie you make, you are trying to convince people that it will be successful. And sometimes you’re right and sometimes you’re wrong. You just hope the ratio is high enough. I think it’s always the case,” said Apatow when we caught up to him at the Hollywood Film Awards. “Usually when they say, ‘What the hell are you doing?,’ they don’t let me do it! I mean, everything is an experiment, so I have a lot of sympathy for them not knowing what will work, or not work. Because I don’t really know, I’m just going with my passion about it.

“I’m glad everybody from Freaks and Geeks is doing well and working. Paul Feig and I really believed in everybody and in that show,” he added. “So we’re proud of everybody, they have fulfilled all of our dreams of what they might do — everybody, all the writers and directors and everybody. And it was less than a season of a show!”

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David Cone
“I think probably it was just committing to the Yankees, embracing that spotlight. It was risk/reward. It’s a hard place to play. I had a chance to be a free agent and I chose to come back to the Yankees in the middle of my career,” said the pitcher at a gala for the organization Safe at Home. “A lot of people thought, ‘Hey, that’s a risky move, New York. The Bronx could eat you up if you don’t play well.’ But, you know, I embraced it and loved it and really reaped the rewards from it.”

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Ai Weiwei
“Many, many situations. You get involved. You feel desperate, you feel this is the end of it and then time passes,” Ai explained at the WSJ Innovator Awards. “Then it’s okay, and you make some improvement or you make consciousness about certain areas. For example, I did research and found over 5,000 students killed by the 2008 Sichuan earthquake — the names, the birthdays. The Chinese state had been refusing to acknowledge those truths that we found one by one through the internet, through film study.”

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Andie MacDowell
“Probably moving to New York when I was 20. I didn’t know anyone, and I moved to New York, and nobody in my family had done anything like that,” said MacDowell at the L’Oréal Women of Worth Awards. “It was pretty crazy and it panned out okay.”

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Matt Ross
“Well, I think a lot of people who make things —- whether you are a painter or a musician — you spend a lot of your life not being financially compensated for your work. The moment that you are is vindication. Being able to get health insurance was a pretty profound and tangible vindication,” said the director at a Peggy Siegal Company-hosted lunch for Captain Fantastic.

“But ultimately, it is not about the money, it is about peer approbation. And I think, as a filmmaker, this journey has been a little bit of that — not exactly vindicated, because vindicated feels like, ‘I was right,’ as if they didn’t believe me. You get to a place where you are at peace with the reality. I have spent a lot of my life feeling like I was an outsider that didn’t get to do the thing I want to do.”

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Megan Hilty
“Going into this business in general,” said Hilty at the Museum of the Moving Image’s annual Salute Gala. “I had teachers that were like, ‘Oh, no you shouldn’t do that.’ I had a lot of people who said, ‘It’s a great hobby, but you shouldn’t do that for a living.’ So, ha ha!”

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Billy Porter
“Everybody in my life, everybody said, ‘It will never work.’ Every single person, even the good ones, even the good ones. You have to ignore them … They said there was no template because I am the template, so I had to do it and create the space so the ones who came behind me can have something to do. The work is the work, the point is, ‘How do I continue to do the work?’ I’m not here to gloat, I’m here to work, so that’s more my MO. Keep doing the work, keep doing things that are perceived to be impossible.”

Did you ever go back to them and tell them how wrong they were?
“I don’t have to, success does that. I don’t have to say anything, because the success of me remaining who I am and pursuing it the way they said wouldn’t work and having it work is all that needs to be said.”

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John Bolton
“I have a degree in journalism, so that whole journey … Deciding to go to New York and try acting before I dove into the rest of my life, which I assumed was going to be journalism. I figured I’d try with no real training. There were a lot of good community theaters in my hometown of Rochester, but I had no real training, so I think I’m proud of the fact that I dove in and I did it,” said Bolton.

“Early on, my mom and dad were always supportive of me — they were wonderful people and I miss them every day of my life. But there were times, a couple of times when — to be supportive — they said, ‘Maybe you should think of doing something that pays you a little more money.’ This was very early, before I even did my first Broadway show.

“Then when I started working regularly they were like, ‘Son of a gun, he’s doing it!’ It was proving to myself that this kid who grew up watching the Tony’s once a year — you had to watch them because there was no video, that was it! — I think to go from those dreams to actually doing it, I’m really, really proud of it. I’m proud of anyone who does that.”

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Dean Winters
“Becoming an actor. My parents were freaked out. I started acting when I was 28 — at that point in your life, you are supposed to know what you are doing. And at 28, I was like, ‘I’m going to become an actor,’ and it took a while to prove to them that I was right. My mom was like, ‘You don’t have insurance!’ And when I finally got my SAG insurance, I think my parents were cool with it. And then they see you on TV and everything is fine.”

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Aaron Eckhart
“Well, I got a film degree in college. And without seeing my diploma — all I had to know was did I do enough courses to get through film school — then the next day I moved to New York City, with $1,300 in my pocket,” said Eckhart at the premiere of Bleed for This hosted by Cinema Society and Men’s Fitness. “I didn’t know anyone, I didn’t have any place to stay, and somehow I got here tonight. I knew what I wanted to do and I believed in myself but, on the other hand, there were no guarantees. So, I would say hands down, that is the riskiest move I made.”

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Peri Gilpin
“Becoming an actress, because it seems like the odds are so impossible and I certainly wasn’t your typical actress-type person. I worked really hard and didn’t stop until I got to do Frasier, so I think that would be my main one,” said Gilpin at the Drama League Benefit Gala Honoring David Hyde Pierce.

“Sometimes people, teachers showing me how to be an actor said, ‘You don’t have the right color eyes’ or ‘you’re the wrong weight’ or ‘you’re not the idea of beauty everyone’s looking for in theater or television or film,’ but my stepdad said something really great. He went, ‘Why not you?’ As bizarre as that is, it was so inspirational to me and I said, ‘Why not?’ I knew I couldn’t do it if I didn’t work hard, I needed to be ready. When the opportunity strikes, I needed to be completely ready, so I really spent a lot of my teens and my 20s studying, interning, apprenticing, doing anything I could in and around theater to build up my résumé, but also to get that experience.

“I got kicked out of college based on a performance, actually. I played Clare in Edward Albee’s A Delicate Balance and she’s a 70-year-old woman who’s an alcoholic and kind of a hot mess. I was 18 or 19 and she was playing an accordion — a very complex character. I was asked to leave my college based on that performance — they didn’t want me, they didn’t think I had the goods, they didn’t want to train me.

“That was like lighting a fire under me, that really did throw down the gauntlet! Then years later, I was telling that story a lot during Frasier. The head of the prop department at the University of Texas wrote me a letter and asked me to stop telling that story — it got back to them. I said, ‘No, no, no, I am going to tell it anytime anyone will listen, so thanks for asking!’

“All this is to say, keep going. If someone’s trying to tell you you need to work on this, you need to improve this, listen to feedback, but don’t ever let anyone tell you you can’t do something.”

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David Hyde Pierce
“Something where people said, ‘No, you can’t do that’ and I said, ‘Yes, I can’? All that comes to mind is people saying, ‘Go for it!’ Everyone was supportive — that’s amazing, especially in a challenging industry,” said Pierce at a Drama League benefit where he was honored. “I’ve been very lucky in that way.” Sure, but that kind of takes the fun out of it.

With reporting by Katie Van Syckle, Josh Grossberg, Ian Goldstein, Vicki Salemi, Jenny Peters, and Fawnia Soo Hoo.

14 Famous People on the Biggest Risks of Their Careers