"Tom, Sarah and Usher" is the 2nd episode of the 2nd season of The Boondocks, and the 17th episode overall. It originally aired on October 15, 2007.
Tom and Sarah DuBois are celebrating their anniversary when Usher shows up. Sarah, being a fan of his, is infatuated with him, causing a rift between her and Tom. This leads to Tom being kicked out and moving in with the Freemans, who plan to help him assert his dominance, with help from A Pimp Named Slipback.
Tom getting kicked out and living at the Freeman's is from the November 2000 storyline of the strip, though there the argument was about Sarah voting for Ralph Nader.
Tropes:
- Animated Musical: Tom sings Usher's "Let It Burn", accompanied by a group of dancers in robes. What's hilarious is that the lyrical version of the song is playing, so Tom sings in conjunction with Usher's vocals.
- Celeb Crush: Sarah has one on Usher, causing tension between her and Tom.
- Comically Missing the Point: A Pimp Named Slickback just can't process that Tom doesn't want to hit a woman.
- "Could Have Avoided This!" Plot: If Tom hadn’t jumped to conclusions and just asked Sarah what was going on, none of this would've happened.
- Didn't Think This Through: The Freeman hire A Pimp Named Slickback to help Tom out with his martial problems, which Tom himself objects to and suggests he just get a regular therapist instead. Robert admits that could've worked, but the plan has already been set in motion.
- Disappointed in You: A Pimp Named Slickback gets this in the end after seeing Tom slap Usher, resulting in him getting beat down on by Usher and his bodyguards. He and his hoe simply leave Tom to his fate, disappointed with his actions.
- Downer Ending: When Tom tries to show Sarah how dominant he is, using his newfound pimp resolve, he instead slaps Usher to keep him from having his wife, only to find out that Sarah brought Jazmine to the hotel because she wanted to see Usher. The thought of cheating was a big misunderstanding. Unfortunately, the slap leads to Usher and his bodyguards giving Tom a No-Holds-Barred Beatdown, and to make matter worse, as Tom is getting beaten, Sarah unhelpfully stands by and pleads with them to stop, while Jazmine cries apologetically, NOT for her own father, but for Usher.
- Emasculated Cuckold: Tom is obviously humiliated with Sarah and Usher openly flirting with each other in the restaurant on their anniversary, to the point even the waiter pities him.
- Fangirl: Both Sarah and Jazmine are huge fans of Usher.
- Feet-First Introduction: Both A Pimp Named Slickback and Sweetest Taboo are introduced with a pan-over shot that starts from their feet.
- Humiliation Conga: Tom is a general Butt-Monkey, but he especially gets put through it in this episode, where even his own daughter doesn't seem to mind about him getting divorced.
- Hypocritical Humor: Robert And Riley after Tom's musical number.Riley: Booooooo! Hey Tom! Shut the fuck up!
Robert: Boy! Watch your mouth! Tom! Shut the fuck up! - It's All About Me: Seriously, Sarah. It's your wedding anniversary dinner and you'd rather leave your husband alone to flirt with Usher instead?
- Well, given that Tom is her husband, Sarah may be right to be unhappy about her marriage. And Tom isn't the most likable husband around, he keeps rambling on about Prison Rape during their anniversary dinner.
- Jerkass Ball: Both Sarah and Jazmine. Sarah for blatantly flirting with Usher in front of Tom and getting mad at him for feeling jealous, and Jazmine for genuinely hoping her parents divorce so Usher can be her "new daddy", being disappointed when it doesn't happen, and crying for Usher when he is beating the ever-living shit out of her father (to be fair, Tom hit him first, but still).
- Lousy Lovers Are Losers: Played for Laughs in "Tom, Sarah and Usher". While Butt-Monkey Tom is thinking back on happy memories of his marriage to Sarah, one of the scenes shows them post-sex, with him collapsing exhausted and sweaty beside her while she has a bored and nonplussed expression, implying she was sexually unsatisfied and he's utterly clueless about it.
- Mistaken for Cheating: Tom thinks Sarah is cheating on him with Usher. Because of the way she acts in this episode, it's hard not to believe why Tom thought that, but when he confronts her about it in the end, he founds out she's meeting with him was so that Jazmine could meet Usher.Tom: So you're not...
Sarah: No... - Musicalis Interruptus: Tom's "Lets it Burn" dance number in the middle of the streets, and he has to stop the music number for a while to let a car pass.
- Modesty Bedsheet: When we see Tom and Sarah after sex, she has a sheet covering her up to the shoulders.
- Ms. Fanservice: Sweetest Taboo, the prostitute A Pimp Named Slickback enlisted to help Tom, is an attractive girl with a midriff-revealing outfit.
- Poor Communication Kills: If Sarah had explained to Tom that she wasn't having an extramarital affair and just wanted to take Jazmine to meet their favorite singer, then most of this episode's conflict would've been resolved much better. Tom isn't entirely blameless either though, he just poorly assumed and never told Sarah what he thought.
- Screw This, I'm Outta Here: Both A Pimp Named Slickback and Sweetest Taboo abandon Tom once he's getting beaten by Usher and his bodyguards.
- There Are No Therapists: Subverted for comedy. When Tom finds out grandpa hired A Pimp Named Slickback to 'help him', Tom says he'd much rather get a normal therapist instead, but goes with A Pimp Named Slickback because grandpa already paid for him (with Tom's credit card).
- The Thing That Would Not Leave: Played for Laughs with the Freemans acting like Tom has been staying with them for weeks and plotting to get him to leave when he's only been there two days.
- Wouldn't Hit a Girl:
- Tom. While A Pimp Named Slickback is teaching Tom on how to assert his dominance over Sarah, he instructs Tom to hit Sweetest Taboo; Tom refuses to do so, and he doesn't even retaliate when she starts beating him up.
- Double Subverted at the end of the episode, when a furious Tom, following A Pimp Named Slickback's teachings, yells at Sarah and commands her to go home with him. He raises up his hand, and at first it looks he's actually going to slap Sarah — but he ends up slapping Usher instead. Tom proves that even at his angriest, he would never lay a hand on a woman, let alone his wife.
