Cleveland realizes that the kid he bullied in high school, "Barry", is the name Barry, who became the President of the United States. Meanwhile, Kenny West is back in town and Rallo is smitten with his daughter, Candice.
Tropes:
- Anachronic Order: Despite the following episode, clearly being the first episode of season two, this aired first.
- Strangely, the Season 2 debut episode makes a callback to this one, when a fan of The Cleveland Show wears a shirt, reading "I Be-Cleve".
- The Cameo: Bruce from Family Guy makes a cameo.Bruce: Whoops, wrong show.
- Continuity Nod: Kenny and Candice West from "Brotherly Love" return.
- Included on the billboard for Top 100 Cartoon Songs, are previous songs from The Cleveland Show, such as "Balls Deep in Love" from "Love Rollercoaster" and "Straight Outta Stoolbend" from "The Cleveland Junior Cherry Bomb".
- I Just Want to Be You: Kenny wanted to be Cleveland.
- One-Hour Work Week: Lampshaded. Cleveland consistently says that he "plain ol' forgot to go to work today".Cleveland: Work! I keep forgetting to go to that!
- Out of Focus: Cleveland Junior had no dialogue in this episode.
- Please, Don't Leave Me: When Obama flew off in his helicopter, Donna jumped up and grabbed onto it, begging him to take her with him.
- Reference Overdosed: The song billboard for Top 100 Cartoon Songs includes tons of songs from other cartoons, including "Bag of Weed" and "You have AIDS" from Family Guy, "The Pecan Sandies Song" from American Dad!, "Boozehound", "Do the Bartman", "We Put the Spring in Springfield", "Baby on Board" and "Who Needs the Kwik-E-Mart?" from The Simpsons, "Blame Canada" and "What Would Brian Boitano Do?" from South Park: Bigger, Longer & Uncut, "Leela: Orphan of the Stars" from Futurama, "Lesbian Seagull" from Beavis And Butthead Do America, "Eep, Opp, Ork, Ah, Ah" from The Jetsons, "Happy Anniversary" and "Happy Housewife" from The Flintstones, "Hello My Baby" from Looney Tunes, "Heffalumps and Woozles" from Winnie the Pooh, the theme song from Hong Kong Phooey, "Hakuna Matata" from The Lion King (1994), "Kiss Dee Girl" from The Little Mermaid (1989), "Somewhere Out There" from An American Tail, the theme song from Anastasia, "Feel Good Inc." by the cartoon band Gorillaz and "Opposites Attract", which is just the mixed media music video of the same name.
- Self-Deprecation: Kanye West starred as himself, going along with a joke, where Cleveland said "Obama doesn't care about black people." This was of course a reference to Kanyegate; an incident at the 2009 VMA Awards, and his infamous statement, "George Bush doesn't care about black people" that he made during an NBC concert as a tribute to those who were lost when Hurricane Katrina devastated New Orleans.
- Who's Laughing Now?: After being tormented and teased by Cleveland all throughout high school, namely for being bad at basketball, Barry grew up to be the 44th President of the United States, and later came back for a basketball rematch with Cleveland, wherein he kicked ... his ... ass. And even then, it's implied that Cleveland actually couldn't beat him, since Obama mentions it as a reason for the chips on his shoulder.
