The Transformation Of Adam Sandler From Teenager To 55 Years Old

Comedian, actor, and producer Adam Sandler has cemented himself as a permanent figure in the comedy world with a career that spans multiple decades. While he is known for his extensive acting résumé today, Sandler had to work hard as a comedian to land his small roles in the late 1980s and early 1990s before his big break on "Saturday Night Live." Throughout the years, generations of people have seen the actor grow through his work, getting his big break on the venerated live sketch show, then moving toward successful feature films, and even creating his own multi-million dollar production company.

There is a reason why the funnyman and his works remain beloved by general audiences and his loyal fans even to this day. Uniquely funny, a little over the top, but always humble, here is the transformation of Adam Sandler from his teenage years to 55 years old.

Growing up, Adam Sandler was inspired by his close-knit family. He always had an interest in comedy, and even used to perform impressions of his own grandmother in front of her and his family. As Sandler shared in a "60 Minutes" interview, his impersonation was always well received. By the time he reached his early adulthood, the actor had his eyes on NYU's Tisch School of the Arts, an institution with notable alumni such as Alec Baldwin and Billy Crystal.

While in college, Sandler worked doing standup at various comedy clubs in New York City, though not everyone was convinced he had what it took to perform as an actor. In Variety's "Actors on Actors," he sat down with fellow star Brad Pitt to discuss their new film roles, finding success in Tinseltown, and the early beginnings of their career.

During the chat, Pitt took the time to share a story he had heard about Sandler regarding a discouraging experience with a college professor. "You were at NYU, and it was your acting coach, or acting professor, I believe," the Oscar winner recalled. "He took you out for a beer and he kindly said to you, 'Think about something else. Listen, you got heart, but you don't have it. Choose another path.'" The "SNL" alum confirmed the story as Pitt was telling it and while the professor may have had their own assumptions, fate and hard work clearly had another plan in mind for Sandler.

Long before his iconic roles in "Billy Madison" and "The Waterboy," Adam Sandler was an aspiring young actor and comedian looking for an opportunity that would help to launch his career. In the 1980s, one of the biggest sitcoms at the time was "The Cosby Show," which starred veteran comedian Bill Cosby with a supporting cast that included Phylicia Rashad and Lisa Bonet. Shortly before graduating from the esteemed NYU Tisch School of the Arts in 1988, he landed a role on the sitcom as Smitty, the best friend of Theo Huxtable in 1987.

While Sandler only appeared in four episodes in the show's fourth season, his onscreen presence and strong characterization of Smitty helped to establish him as an actor and lay the foundation for the successful career he would have in the future.

During his run on "The Cosby Show," Sandler received advice from Cosby himself about one thing to do as a comedian. In an interview with The Grio (via NBC News), the actor said, "I was just a kid ... I was only like 18 or something. But he just told me that, 'You should just try to keep it clean when you do your acting, think about if it's necessary to use that curse or not.'" Sandler further noted that while he was unfiltered and loose with his language in his early standup, he applied Cosby's advice to his later career, using minimal cursing in his films.

Just three years after his run on "The Cosby Show," Adam Sandler secured the ultimate gig for any comedian, a role on "Saturday Night Live." After having a handful of small roles in various movies, the actor landed a recurring position on the beloved live comedy sketch show in 1990 when he was in his early 20s. On the show, Sandler performed alongside comedy greats like Dana Carvey, Phil Hartman, Chris Farley, and David Spade, who were all main cast members at the time.

During his stint on "SNL," the comedian had many iconic roles and funny bits, which included a recurring sketch with Spade and Farley called "Gap Girls" as well as a character called "Canteen Boy." The titular character from the latter would later inspire the Sandler flick "The Waterboy," per CNN. Though Sandler's contributions were well received at the time, his run would come to an end five years after he became an official cast member.

According to the Daily Beast, Sandler parted ways with "SNL" in 1995 along with fellow member and friend Chris Farley. "We kind of quit at the same time as being fired. It was the end of the run for us. The fact that me and him got fired? Who knows. We were on it for a few years, had our run, and everything happens for a reason," Sandler told the outlet. Despite this, the comedian went on to have a successful film career that would dominate the next two decades.

Movies are arguably what Adam Sandler is most recognized for, but his work making comedy albums is also popular among fans, especially during the holiday season. The comedian wrote "The Thanksgiving Song" while he was a regular on "Saturday Night Live" back in 1992. The song, which originally appeared on the sketch "Weekend Update," would later be released on his debut album "They're All Gonna Laugh At You!" in 1993, per Rolling Stone. Despite being a humorous song about the sometimes absurd spectacle of the Thanksgiving holiday, Sandler's song was a hit among listeners and even spent two weeks at the number 37 spot on the Billboard Active Rock chart in December 1998, per Billboard.

Fans of Sandler may know of "The Thanksgiving Song," but his hit "The Chanukah Song" reached listeners everywhere. Like its holiday-themed predecessor, "The Chanukah Song" debuted on "Saturday Night Live" during the "Weekend Update" sketch in 1994. In the song, the comedian talks about the overbearing nature of Christmastime and how it can be particularly hard for Jewish people. Sandler released the song two years later on the album "What the Hell Happened to Me?" which peaked at number 80 on the Billboard Hot 100 chart in January 1999, according to Billboard.

Adam Sandler has also found incredible success making comedy albums. During his gig on "Saturday Night Live," Sandler released standup debut "They're All Gonna Laugh at You!" in 1993. The album features 22 original songs by the comedian, which includes his iconic hit "The Thanksgiving Song," among other songs and comedy recordings.

Despite being known for his silly but arguably clean humor, Sandler's style on the album is explicit and filled with plenty of adult content. "They're All Gonna Laugh At You!" also happens to be a star-studded record with performances by Conan O'Brien, David Spade, Tim Meadows, and so on. On creating the album, Sandler told Spin in 2013, "There were skits and songs and stuff I wanted to do but didn't think I could get on SNL because they were too filthy. ... Everyone thought I wanted to make a stand-up record, but I wanted to do something more like Cheech & Chong, with sketches and everything. That was the idea."

Three years after his debut album, the comedian released "What the Hell Happened to Me?" in 1996. Sandler's second comedy album features his memorable "The Chanukah Song" as well as "Ode to My Car," both of which are fan favorites. Both albums have both sold over two million copies and are certified double platinum, per AV Club.

Adam Sandler's departure from "SNL" didn't discourage him from pursuing a career in comedy. The same year he left the series, Sandler co-wrote and starred in "Billy Madison," which he had the lead role in. The following year, in 1996, he once again utilized his creativity and co-wrote "Happy Gilmore," a film that he also starred in. Both films were incredibly successful at the time, with "Billy Madison" grossing over $25 million worldwide, and "Happy Gilmore" earning almost $39 million.

By the late 1990s, Sandler soared further in the movie industry, and decided to start his own production company. The actor created Happy Madison Productions in 1999 after producing both "The Waterboy" in 1998 and "Big Daddy" in 1999. According to Far Out, Sandler founded the company with Jack Giarraputo, who had a hand in some of Sandler's earlier works like "Billy Madison." The first film officially under the company's belt was "Deuce Bigalow: Male Gigolo," which was released in 1999.

While Sandler's films have not always been highly regarded by the industry's critics, they nonetheless have become fan favorites over the years and garnered billions in revenue. Since its start over 20 years ago, Happy Madison Productions produced nearly 50 films, which as of 2022, totaled $3.9 billion in revenue, as reported by The Numbers.

While Adam Sandler may be one of the biggest comedians in the film industry, unlike some of his celebrity peers, he keeps personal and romantic life relatively private. As the actor was filming 1999 comedy "Big Daddy," he met Jackie Titone, who at the time was a model, according to the Daily Mail. In the film, Titone appears as a waitress in a scene with little Julian (Cole Sprouse and Dylan Sprouse) that lasts less than 30 seconds, but her presence was enough to make an impression on Sandler. In 2020, the "Happy Gilmore" star shared pictures on Instagram of the pair together from around the time they first met and revealed they had an instant connection. "22 years ago today we locked eyes and fell deep. Look forward to the next 22, young lady. Love you my forever girl," he wrote.

The couple married in June 2003 and prior to their religious ceremony, Titone converted to Judaism, as reported by People. Three years after they tied the knot, the pair had their first child, a daughter named Sadie in 2006, followed by a daughter named Sunny in 2008, per The Sun.

After meeting Sandler, Titone continued to act in a number of his films, including, "Little Nicky" and "50 First Dates," according to her IMDb page.

When the name Adam Sandler comes up, serious flicks are not what typically comes to mind. That said, while his career has mainly centered around humorous fare, Sandler has not shied away from taking on heavier roles in drama films. In 2002, he starred in Paul Thomas Anderson's "Punch-Drunk Love," alongside Emily Watson and Philip Seymour Hoffman. The movie centers around Barry Egan (Sandler), a man whose life gets turned upside down after he makes a call to a phone sex line, jeopardizing his job and those he loves. Sandler brings his comedic edge to "Punch-Drunk Love," but also delivers a complex, emotional performance that instantly drew in viewers and garnered a certified fresh rating on Rotten Tomatoes.

The actor continued to dominate the comedy movie genre in the 2000s, but he returned to drama in the 2007 film "Reign Over Me." Directed by Mike Binder and starring Don Cheadle, the movie follows estranged friends Charlie Fineman (Sandler) and Alan Johnson (Cheadle) as they deal with the aftermath of the September 11 attacks. The feature earned a certified fresh rating on Rotten Tomatoes, with critics praising Sandler's intimate, complicated portrayal of a man stuck in his own grief.

Sandler's latest dramatic role was in the 2019 film "Uncut Gems" directed by the Safdie Brothers. "Uncut Gems" received widespread acclaim, and in 2020, the actor won the Independent Spirit Award for Best Male Lead, per The Independent.

Adam Sandler has not slowed down when it comes to making movies. In 2014, he signed a deal with Netflix, which was later renewed in 2017. The terms of the deal detailed that Sandler would make four films and get $250 million for his work, as reported by Forbes. While his films on Netflix have not always received good reviews from critics, they have remained loved by fans of Sandler's work.

In 2019, he starred in the Netflix film "Murder Mystery" alongside actor Jennifer Aniston, which was a hit when it dropped. According to the AP, the movie was the most popular on the streaming platform in the United States, and among the most popular around the world. Because the incredible success of "Murder Mystery," he secured another deal extension with Netflix in 2020, agreeing to make an additional four movies, per Insider.

Since signing the deal, the actor and producer has released one movie on the streaming service: 2020's "Hubie Halloween," and "Hustle," which will be released on Netflix on June 3, 2022, per The Philadelphia Inquirer.

Throughout his professional career, Adam Sandler has formed a number of friendships with other stars. And those friendships have stood the test of time. 

While Sandler was on "SNL," he became good pals with fellow cast members David Spade and Rob Schneider, both of whom have appeared in a lot of Sandler movies. Sandler has also produced movies that his good pals were in, such as Schneider's 1999 comedy, "Deuce Bigalow: Male Gigolo," or Spade's 2001 film, "Joe Dirt." In a 2020 interview on Rob Lowe's podcast, "Literally! With Rob Lowe," Spade touched on just how close the two are when it comes to professional collaborations. He said, "I've probably only been in about 40 [Adam Sandler movies], I mean, I sort of come in the fine print, you know what I mean?"

Another buddy and frequent costar of Sandler's is actor Drew Barrymore. The two first worked together on 1998's "The Wedding Singer," and ever since, they have stayed friends and worked on other movies, including "50 First Dates" and "Blended." And all these years later, it's clear these two have a strong bond. Per People, when Barrymore presented Sandler with an award at the 2020 National Board of Review Annual Awards Gala, she said, "You deserve the best, you give the best, and you are the best. I love you very much."

Thanks to his various acting roles, writing gigs, and film production work, this "Saturday Night Live" alum has raked in a lot of dough over the course of his career. According to Celebrity Net Worth, as of 2022, Adam Sandler is worth a whopping $420 million, with a fixed $20 million salary per each of his movies.

When his movie career was taking off, Sandler didn't quite have the celebrity status or income he holds today, but he was still making millions for his roles. For "Billy Madison," the actor earned $1.7 million, which he similarly brought in for his later gig in "Happy Gilmore."

The exact number Sandler earns for each of his roles depends on the film and its distribution company. Forbes reported in 2020 that his deal with Netflix helped to boost his income significantly, while his part in "Uncut Gems" paid him $5 million. Per Newsweek, Adam Sandler has become one of the richest actors in the world. Needless to say, he doesn't have to worry about denting any cans.