Adam Sandler's Movie Disaster Timeline

adam sandler that's my boy

Photo: YouTube screengrab

Remember when Adam Sandler movies used to be good? Funny? Perhaps slightly amusing? Sandler had a string of classic films in the ’90s that replay over and over on cable television—”Happy Gilmore,” “The Waterboy,” “The Wedding Singer,” (which gave us Julia Guglia,) and, of course, “Billy Madison.”

However, after “Big Daddy” in 1999, Sandler’s films started to slide. 

See how Sandler lost his funny bone on screen >
While some of his films may have been box office successes; the mere quality started venturing downhill bringing into question whether the films even deserved their blockbuster status.

Granted, there were still some enjoyable flicks in between (“Anger Management”), but in trying to branch out of his tired SNL comedic routine and tackle more serious themes including fatherhood and death (“Spanglish,” “Reign Over Me”) he missed the mark with fans.

billy madison

Photo: Moviesinla via Flickr

So, he returned to his juvenile brand of comedy; however, once Sandler attempted becoming a more serious actor, audiences weren’t having that either (“You Don’t Mess With the Zohan,” anyone?). 

After this, Sandler tried his luck with Disney’s more family-friendly “Bedtime Stories” before shacking up onscreen with fellow comedians (“Grown Ups”).

When that became a success, he immediately went back to his slapstick comedy routine with feeble jokes in “Jack and Jill.” 

The thing with Sandler is that he moves one step forward and two steps back with films. Now, fans are so used to the gimmicky brand of Sandler folly, that we kind of just go with it

With the outwardly outrageous looking “That’s My Boy” out Friday, let’s take a walk down memory lane at Sandler’s films.

Opening Weekend: $16 million
Domestic: $39.4 million
Worldwide: $58.2 million
Budget: $85 million
Rotten Tomatoes Score: 22% / 64%*

Sandler starred as the oddball son of Satan in the box office flop he also wrote and co-produced. The film dipped more than 51 per cent during week two in theatres.

(Box Office Mojo)

*Note: Percentages represent critic's and audience review scores respectively.

'Punch Drunk Love' Worldwide: $24.6 million
'Mr Deeds' Worldwide: $171.2 million / Budget: $50 million
'Anger Management' Worldwide: $195.7 million / Budget: $75 million
'50 First Dates' Worldwide: $196.4 million / Budget: $75 million

With an original limited release, 'Punch-Drunk Love' never really picked up off the ground until it's wide release three weeks later. The film saw two weeks in the bottom of the top 10 before bowing out. The R-rated romantic comedy grossed $24.6 million worldwide.

Opening Weekend: $8.8 million
Domestic: $42.7 million
Worldwide: $55 million
Budget: $80 million
Rotten Tomatoes Score: 53%/63%

After a few funny films, Sandler once again set his sights on a more somber role in the dramedy starring Téa Leoni and Paz Vega. The film didn't go over so well with a meager box office debut of $8.8 million. With a short seven weeks in theatres, it was clear fans weren't keen for a more serious Sandler.

(Box Office Mojo)

Opening Weekend: $47.6 million
Domestic: $158.1 million
Worldwide: $190.3 million
Budget: $82 million
Rotten Tomatoes Score: 31% / 67%

The quirky remake of the 1974 original by the same name wasn't Sandler's worst film--it stayed among the top 10 for six weeks. Though the film was a far cry from the original, even Roger Ebert was (slightly) amused by the remake … the first time he saw it.

(Box Office Mojo)

Opening Weekend: $40 million
Domestic: $137.3 million
Worldwide: $237.6 million
Budget: $82.5 million
Rotten Tomatoes Score: 33% / 72 %

The film about a workaholic father who gets a remote control to fast-forward through the boring parts of life was well-received by audiences, but took a hard hit from critics. The stuffed-animal-molesting dog bit did get to be a bit much after the first two times.

(Box Office Mojo)

Opening Weekend: $7.4 million
Domestic: $19.6 million
Worldwide: $22.2 million
Budget: $20 million
Rotten Tomatoes Score: 63%/81%

Sandler's attempt at a more somber role where he played a man who lost his family on 9/11, seriously backfired. Despite Don Cheadle starring alongside him and decent reviews, the film had a short six-week run in theatres after it quickly plummeted on the box office list to the 42 spot. 'Reign Over Me' failed to meet its production budget of $20 million in the U.S.

From the trailer, the movie originally looked like it was supposed to be serious with funny undertones given Sandler uses a variation of his silly voice reserved for characters including Bobby from 'The Waterboy.' It's at the second half of the trailer we're finally provided with a glimpse of the real film: an ultimately dark, depressing mantra--a far cry from Sandler's usual brand of films.

Opening Weekend: $34.2 million
Domestic: $120 million
Worldwide: $186 million
Budget: $85 million
Rotten Tomatoes Score: 14%/ 73%

Sandler and Kevin James ('King of Queens' fame) play two firefighters, Chuck and Larry respectively, who wed in order to receive partner benefits. The film spent a solid five weeks in the box office top 10.

(Box Office Mojo)

Opening Weekend: $38.5 million
Domestic: $100 million
Worldwide: $199.9 million
Budget: $90 million
Rotten Tomatoes Score: 37%/50%

In what we could have mistaken for a Sacha Baron Cohen bit, Sandler decided to return to the bizarre in his next film where titular character (Zohan) fakes his own death to live out his dream of becoming a hairstylist in New York City. The premise gets old, quick. After three weekends earning above $7 million at the box office, the fashion film slowly fizzled out.

(Box Office Mojo)

Opening Weekend: $27.4 million
Domestic: $110.1 million
Worldwide: $212.8 million
Budget: $80 million
Rotten Tomatoes Score: 25%/63%

Despite earning $110.1 domestically, 'Stories' put us--and audiences--to sleep. It's no surprise the film did so well given it was one of three films family movies released during the 2009 holiday season (the others being 'The Tale of Despereaux' and 'Marley and Me'). The film was knocked from the box office top 10 quickly, dropping nearly six spots weekly in theatres.

(Box Office Mojo)

Opening Weekend: $22.6 million
Domestic: $51.8 million
Worldwide: $71.5 million
Budget: $75 million
Rotten Tomatoes: 68%/58%

Though filled with Seth Rogan, Jonah Hill and Jason Schwartzman, the dramedy was overtly unfunny despite a deceptively humorous trailer. The movie followed the lead's (Sandler) diagnosis with a rare blood disorder and ensuing (depressing) aftermath.

(Box Office Mojo)

Opening Weekend: 40.5 million
Domestic: $162 million
Worldwide: 271.4 million
Budget: $80 million
Rotten Tomatoes: 10%/59%

After flop 'Funny People,' Sandler included actual funny people, Chris Rock, Kevin James, David Spade and the always present Rob Schneider in his next film. Despite poor critic reviews, the film saw box office success, enough to warrant a sequel.

'Grown Ups 2' is currently set for release in July 2013.

(Box Office Mojo)

Opening Weekend: $30.5 million
Domestic: $103 million
Worldwide: $214.9 million
Budget: $80 million
Rotten Tomatoes: 19%/62%

No doubt injecting model Brooklyn Decker (and surprise role with Nicole Kidman) helped give the film an added boost at theatres. However, big cameos couldn't save the film whose humour (or lack thereof) fell flat as a result of Decker's killer looks stealing the spotlight. We also couldn't get over Aniston's 'daughter' with the fake British accent.

(Box Office Mojo)

Opening Weekend: $25 million
Domestic: $74.1 million
Worldwide: $149.6 million
Budget: $79 million
Rotten Tomatoes: 3%/39%

(Box Office Mojo)

After Sandler's earlier box office hit last year, it appeared the comedian was heading in the right direction ... and then this happened.

Sandler teamed up with himself to bring disastrous 'Jack and Jill' to theatres. Sandler played both twins Jack and obnoxious sibling Jill Sadelstein. The film didn't surpass its production budget of $79 million after a 16-week run in theatres.

The film retained a three per cent rating on Rotten Tomatoes--one of the lowest scores of 2011. In addition, Sandler's comedy swept the Razzies, the annual award show honouring Hollywood's worst movies, winning every award--a first in the show's history, all but solidifying how far the comedian has fallen from his glory days.

Just when we thought he couldn't out do himself, 'That's My Boy' comes along. When we saw the first trailer, we must admit, we thought (hoped? prayed?) it was a farce ... a 'Funny or Die' parody at best.

This may be the most ridiculous plot line Sandler has delivered since ... well, his last film. Looking like Robbie Hart of 'The Wedding Singer,' the film follows Sandler reuniting with his long lost son who he fathered as a teenager.

Now that Andy Samberg is officially out of SNL, that will surely help draw audiences. However, from watching the trailer, the film looks like it will be shrouded with juvenile humour which doesn't seem to resonate with fans who have grown up with Sandler's films anymore. While they have matured, Sandler's brand of humour has failed to evolve with them.

Enough Sandler films, now let's talk superheroes.

NOW WATCH: Briefing videos

Business Insider Emails & Alerts

Site highlights each day to your inbox.

Follow Business Insider Australia on Facebook, Twitter, LinkedIn, and Instagram.