There is no denying that Adam Sandler has had one of the biggest reinventions in Hollywood, transforming his career from a few small roles into the undisputed king of comedy.
The 58-year-old is undoubtedly one of busiest stars around, having made his screen debut in the 80s, and is still working tirelessly today.
On Friday, he is set to bring a beloved character back to our screens once again in the Happy Gilmore 2 sequel, leading the star-studded cast alongside Julie Bowen, Christopher McDonald and Ben Stiller, with appearances from Travis Kelce and Bad Bunny.
But how did the Brooklyn-born actor, who made us all laugh in Just Go With It, Big Daddy and Grown Ups, into a multi-million-dollar deal with Netflix and so much more?
Adam began his career in stand-up before making the transition over to the small screen, with his TV debut as Smitty in a handful of episodes on the Cosby show in 1987.
From there, he landed a string of film roles in movies including Going Overboard and Coneheads, before becoming a regular on Saturday Night Live between 1990 – 1995.
He also starred in and wrote Billy Madison and Happy Gilmore, as well as showcasing his talents in Big Daddy, Little Nicky, The Hot Chick, 50 First Dates and many more.
Over the last few years, he has juggled his regular comedies in with some more serious roles, including Uncut Gems, Hustle and Spaceman, and is set to star opposite Laura Dern and George Clooney in Jay Kelly very soon.
In 2014, his Happy Madison company took a huge step and signed a massive deal with Netflix, worth $250million, to produce films for the streaming service, including The Ridiculous 6, The Do-Over and his Murder Mystery movies.
He also headlined two Netflix stand-up specials, 100% Fresh and I Love You.
The lucrative partnership with the streaming services has been extended twice so far and, according to the Telegraph, in 2020, Netflix bosses claimed that subscribers had spent more than two billion hours watching his films.
This has all helped to cement his status as one of the biggest stars of our time. Forbes reports that he was the 9th highest paid actor for 2024 – after topping the annual list the previous year – and earned a whopping $26m.
Considering he has two huge projects coming out this year and a reported net worth of around $440m, we predict more appearances in the Forbes list in his future…
While Adam has remained booked and busy in the decades since his career began, he has also gone above and beyond to help out his peers in the industry, giving pals roles and cameos in whatever project he was working on.
In fact, members of his circle have become his most regular co-stars, with Rob Schneider, Steve Buscemi and David Spade appearing in countless Adam Sandler creations alongside his wife, Jackie, and their daughters, Sadie and Sunny.
Hollywood heavyweight Al Pacino previously shared that the Funny People superstar gave him a role in 2011’s Jack and Jill at a point when he was struggling for money – due to a corrupt accountant and years of overspending.
‘I was broke. I had $50 million, and then I had nothing,’ he wrote in his 2024 memoir, Sonny Boy, via IndieWire. ‘In this business, when you make $10m for a film, it’s not $10m. Because after the lawyers, and the agents, and the publicist, and the government, it’s not $10m, it’s $4.5m in your pocket.
‘But you’re living above that because you’re high on the hog. And that’s how you lose it. It’s very strange, the way it happens. The more money you make, the less you have.
‘The kind of money I was spending and where it was going was just a crazy montage of loss. […] And I thought, It’s simple. It’s clear. I just know this. Time stopped. I am f**ked.’
‘Jack and Jill was the first film I made after I lost my money. To be honest, I did it because I didn’t have anything else,’ he recalled. ‘Adam Sandler wanted me, and they paid me a lot for it. So I went out and did it, and it helped.
‘I love Adam, he was wonderful to work with and has become a dear friend. He also just happens to be a great actor and a hell of a guy.’
There is no denying that Adam has been a major part of the most iconic comedies in recent years, with many of his early 00s films still being quoted today – but he hasn’t always been taken seriously by critics.
In fact, while he pocketed millions of dollars in his deal with Netflix, he also has nine Razzies to his name and many more nominations.
Discussing the harsh criticism he has received throughout his career and whether that ‘stings’, he told the AARP: ‘Sometimes. Mostly because I invite all these amazing people I care about to make movies with me, and I wish they didn’t have to read s**t about whatever we’ve made.
‘But I don’t get too shook up. I always remember something my father said. He was a tough b*****d. He went through ups and downs in his life, like not having work for a year or two and not telling us.
‘I recall one time that something didn’t go right for me. I bombed onstage or didn’t get an audition. I was upset and probably embarrassed. And he said, “Adam, you can’t always be happy. People aren’t always going to like you. You’re going to fail.” I said, “But I just want to be happy, man. I don’t want all that other crap.”
‘He said, “You won’t actually know you’re happy if you don’t feel that other stuff.”
Touching on what keeps him going amid negative reactions, he added: ‘I like giving myself over to a new challenge. Sometimes I feel like I’m tapped out with new thoughts, and then all of a sudden, something new comes up and I go, “Okay, how can I make this happen?”
‘It was cool as hell pushing myself in new ways like I did on Uncut Gems. Running around the Diamond District in New York, the intensity of that amazing character, or in Hustle, being around the greatest NBA players and not worrying about laughs as much as what each character is going through and pulling for. But I do love comedy more than anything.’
Happy Gilmore 2 is released on Netflix on Friday.
Got a story?
If you’ve got a celebrity story, video or pictures get in touch with the Metro.co.uk entertainment team by emailing us celebtips@metro.co.uk, calling 020 3615 2145 or by visiting our Submit Stuff page – we’d love to hear from you.
