|The Cleveland Show episode|
|Episode no.|| Season 1|
|Written by||Justin Heimberg|
|Directed by||Anthony Agrusa|
|Guest stars||Kanye West as Kenny West|
Taraji P. Henson as Chanel Williams
Jason Alexander as Saul Friedman
Bebe Neuwirth as Sarah Friedman
|Original airdate||May 2, 2010|
|List of The Cleveland Show episodes|
Acting as his stepbrother's wingman, Rallo gives Cleveland Jr. a few pointers on how to win over the girl of his dreams, Chanel Williams (guest voice Taraji P. Henson) but Rallo after saying he would like more mature women then falls for Chanel but she sees him as a baby. Although when Cleveland Jr. finds out her boyfriend is local rap star Kenny West (voiced by Kanye West in a self-parody), Cleveland challenges Kenny to a rap battle to win Chanel's heart, the rap battle ends with Junior and Kenny admitting they are equally good and Junior letting Kenny have Chanel as Chanel and Kenny have a child together.
In a side story Terry becomes a stripper, with Cleveland as his manager. Then Terry starts having sex with the women he strips for, making him a prostitute. Cleveland then becomes his pimp.
- Bone Density Machine Sales Job by Kenny West is a reference to The Pursuit of Happyness in which Garner sells Bone Density Machines for a living.
- After Cleveland Jr. first rhymes he finishes with a reference directly quoted from the film 8 Mile.
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