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"Give me a kiss!"
~ The Sheriff shamelessly flirting with Kate in his drunken lust for her as she pleads help for Sam's life
The Sheriff is a posthumous supporting antagonist of Disney's Holes. After refusing to save Kissin' Kate's boyfriend's life then attempting to force himself on her, his actions are one of such that lead to her beloved's death and cause Kissin' Kate to retaliate and kill the men responsible, causing the Sheriff to be the first to be killed for his crimes. He is portrayed by actor Eric Pierpoint.
While getting drunk for an occasion, Katherine Barlow entered the Sheriff's office in a tearful frenzy, begging him to stop the angry mob and save the schoolhouse. However, the Sheriff did nothing to help her situation and instead focused on how beautiful she was and was determined to act on his lust for her. The Sheriff put down his drink and asked Katherine for a kiss, reminding her that she kissed the onion picker Sam. Katherine was disgusted by his actions and pushed his arm off of her while reminding him that he is drunk. Rejected, the Sheriff laughs and says that he always get drunk before a hanging. Katherine at first confused by his remark then figures out what he was planning to do to Sam. As the Sheriff crept closer to her to try kissing her again, Katherine told him that if he kills the man she loves, then she'd rather hanged too and die with her beloved because she kissed him back. The Sheriff rebuffs her need, telling her in his belief though it's not illegal for her to kiss him; that it was illegal for Sam to kiss her, he once again refuses to help her and tries to kiss her again, this time forcing himself onto her. However, Katherine bravely pushes him away in her attempt to save Sam's life. However, it was too late for Sam was killed by Trout in front of Kathrine's eyes.
Heartbroken at Sam's death, Kate decided to kill all the men starting with the Sheriff for he refused to save Sam's life and instead lusted after Kate in his drunkenness. The day after Sam's death, the Sheriff was in his office suffering from a hangover when Katherine walked in looking beautiful dressed in red clothing. Though surprised at Kate for entering his office after her rejection of him last night, he anticipated his excitement for her. As Kate removed her hat tearfully, she asked the Sheriff if he still wanted that kiss he asked for last night. The Sheriff, once again acting on his lust for her, gave her a smirk and awaited his kiss. However, his anticipation turned into disaster when Kate quickly pulled out her gun, aimed towards his face and shot him to death. She then planted a fresh lipstick kiss-print on his deceased face before leaving, and his dishonorable death would cause the killing spree of outlaw Kissin' Kate Barlow.
The Sheriff is revealed to be intoxicated a lot, especially at times when someone is going to be hanged or killed for his/her crimes. He also holds a contradictory belief that it is legal for a Caucasian woman to kiss a African-American man but that its illegal for an African-American man to kiss a Caucasian woman, and its because of such belief that he refuses to save Sam's life for Kate's sake. It's because of this that he gets killed first by Kissin' Kate Barlow the next day.
"Ooh, I love peaches!"
~ The Sheriff addressing Kate's famous spiced peaches in his lust after her
"Give me a kiss."
~ The Sheriff refusing Kate's call for help
"You kissed the onion picker."
~ The Sheriff teasing Kate for a kiss since she kissed Sam earlier
"I always get drunk before a hanging!"
~ The Sheriff telling his reason for being drunk when she rejects him
"Ain't against the law for YOU to kiss him..."
~ The Sheriff disagreeing with Kate's plea to die by her beloved's side in the hanging
"...Just against the law for HIM to kiss you!"
~ The Sheriff's last words as he rejects Kate's plea to save Sam's life and tries to force himself onto her
He's the first man to be killed by Kissin' Kate Barlow, as he's one of many men responsible for her beloved Sam's death.
The Sheriff getting drunk
The Sheriff asks Kate for a kiss instead
The Sheriff taunting Kate of her kissing Sam
The Sheriff touching Kate innapropriately
The Sheriff tells her how he always gets drunk before a hanging
"Ain't against the law for you to kiss him..."
"It's against the law for someone like him to kiss you!"
The Sheriff tries to kiss her against her will
The Sheriff forcing himself on Kate before she pushes him away
The Sheriff in his hangover when he sees Kate
The Sheriff smirking as he awaits his kiss with Kate
The Sheriff's shocked look on his face when he sees Kissin' Kate's gun