Adam Sandler’s everyman charms have made him one of the most beloved movie stars in Hollywood. But he doesn’t always play a lovable goofball that the audience can root for. The Sandman often plays characters with serious anger issues or characters who constantly lie to people or immature characters who are stuck in a state of arrested development.
Some of Sandler’s characters, like hopeless romantic Robbie Hart and unwavering do-gooder Longfellow Deeds, are more likable than others, like serial manipulator Dr. Danny Maccabee and self-serving disgraced quarterback Paul “Wrecking” Crewe.
Dr. Danny Maccabee
In the romantic comedy Just Go with It, plastic surgeon Dr. Danny Maccabee lies to women so he can have sex without making any commitments. He wears a wedding ring and makes up sob stories about being in a terrible marriage so women will feel sorry for him and sleep with him.
Danny keeps the lie going when a woman he really likes finds his fake ring. He recruits his assistant and her kids to pretend to be his family. The lengths he’ll go to in order to deceive women are astounding (and sleazy).
Paul “Wrecking” Crewe
Sandler took on Burt Reynolds’ role in the remake of The Longest Yard. Paul “Wrecking” Crewe is a disgraced former NFL star who thinks the world revolves around him. At the beginning of the movie, after being politely asked to engage with a party, Paul steals his girlfriend’s car, smashes it up, and takes the police on a wild goose chase.
The character becomes slightly more likable behind bars as he assembles a football team made up of his fellow inmates and starts acting selflessly for the good of the team.
Billy Madison
The title character in Billy Madison is a spoilt rich kid. He’s the heir to a Fortune 500 corporation who enjoys a life of ludicrous luxury, and yet he never worked a day in his life.
Billy didn’t even finish his grade 1-12 education – the only work that people are legally required to do – until he was forced to go back to school at age 27 to prove he was competent enough to run his father’s company.
Howard Ratner
Sandler gave one of his finest dramatic performances in the Safdie brothers’ intense crime thriller Uncut Gems. Howard Ratner is a self-destructive gambling addict who can’t help himself. Even when he’s ahead, he doubles down.
Howard sees himself as an underdog. As he explains to Kevin Garnett, “This is how I win.” He drives away everyone who cares about him, from his wife to his mistress.
Happy Gilmore
The title character in Happy Gilmore is extremely volatile. He acts before he thinks and resorts to violence at the drop of a dime. When he believes his caddy is stealing his clubs, he punches the poor kid in the face.
Still, Happy’s love for his grandma makes him endearing. He’s only competing in a golf tournament to save his grandma’s house from being repossessed. His selflessness makes him likable.
Barry Egan
Paul Thomas Anderson gave Sandler his first acclaimed dramatic role in Punch-Drunk Love. Barry Egan is a loner who longs for company and affection but doesn’t know how to get it.
He’s mentally unstable, owing to severe emotional issues, and he’s mercilessly bullied by his overbearing sisters. Barry is more pitiable than likable, but he starts to stand up for himself after finally finding love with his sister’s co-worker Lena.
Jill Sadelstein
Sandler played both titular roles in Jack and Jill. Jack is an ad executive and Jill is his lonely twin sister. Jill has no friends and her brother only invites her over at Thanksgiving.
She’s perceived as annoying due to her loud mouth, her oddball personality, and her dramatic overreactions, but she means well. Jill never intentionally hurts anyone’s feelings; she’s kind and caring and she always has people’s best interests at heart.
Sonny Koufax
In Big Daddy, Sandler plays underachiever Sonny Koufax, who takes in his roommate’s estranged son. At first, he just agrees to look after him until a foster family can be secured. But he ends up loving the kid like he’s his own son.
Sonny goes to court to fight for the right to become the boy’s legal guardian. This is one of the best examples of a Sandler man-child character learning from his mistakes and growing into a more mature, responsible person.
Robbie Hart
There’s a bittersweet irony in the characterization of the eponymous wedding singer in Sandler’s first romcom, The Wedding Singer. Robbie Hart is a hopeless romantic who sings at other people’s weddings but can’t find love in his own life.
His prayers seem to be answered when he falls for a sweet-natured waitress played by Drew Barrymore. The only problem is, she’s engaged to a philandering jerk.
Longfellow Deeds
Sandler played the title character in Mr. Deeds, a remake of Frank Capra’s 1936 classic Mr. Deeds Goes to Town, which was based on Clarence Budington Kelland’s 1935 short story Opera Hat.
Longfellow Deeds is easily Sandler’s most likable character. He can’t help but do good. He never thinks about himself and always thinks about other people. Deeds inherits a fortune from a distant relative, but he doesn’t want a penny of it. He treats his servants as equals and lets homeless people use his shower.
