|Gabriel "Federline Jones" Friedman|
|Voiced by||Jamie Kennedy|
Gabriel Friedman, more commonly known as Federline Jones, is Roberta's Jewish boyfriend and classmate. He appeared in the "Pilot", where Cleveland made sure that Federline brought Roberta home at exactly 10:00pm. Cleveland has since loosened this curfew, agreeing to let Roberta come home at midnight in exchange for Federline helping Cleveland Jr. with the ladies. In "The One About Friends", Roberta wanted Federline to be allowed move into the Browns-Tubbs's house, if Ernie was allowed to move in. Federline appears to only be dating Roberta for her body, believing that it doesn't matter if she is smart as long as she is physically attractive.
In "A Brown Thanksgiving", he spends Thanksgiving with Roberta. However, things take a turn for the worse when two hobos steal his car, a Oldsmobile Cutlass. He manages to retrieve it at the soup kitchen, where he learns that family is the most important thing of all.
Further referencing Kevin Federline, Federline enjoys rap and hip-hop, described by Cleveland as a lame, inside-out oreo, overall a stereotypical wigger. His catchphrase involves him rhyming something with "flip", such as "script", followed by a high pitched sound similar to a siren. His rapping skills are apparently not very good, getting beaten up at T.G.I. Cheney's for playing one of his recordings. Nevertheless, he has released at least one CD, titled "Fireman Killer". Though due to his rapper lifestyle, his parents, both of whom are professors, appear to hold a deep disdain towards him which they hide behind a supportive parent facade.
His real name was revealed to be Gabriel Friedman in "Brotherly Love".
In "Love Rollercoaster" he admits he only dates Roberta for her body. Though for some reason despite knowing this, Roberta continues to date him. However, Roberta broke up and subsequently made up with him in "How Do You Solve a Problem Like Roberta?". In another example of Roberta's fickleness, she decides to pursue both Edwin Mullins and then Caleb while Federline studies for his SAT tests in "Nightmare on Grace Street".
Federline's parents Sarah and Saul bump into Federline and Roberta in "B.M.O.C." as they try to ditch Cleveland at State College where they teach and give them the tour, impressed with the assumption that Roberta convinced Federline to attend college.
Federline and his father sit in The Broken Stool planning Thanksgiving in "Turkey Pot Die" and is inexplicably dressed similar to Abraham Lincoln during "Anny the Musical" in "A Vas Deferens Between Men & Women".
He has a cameo in the crowd at the school diving competition in "The Hangover Part Tubbs".
- TCS101 Pilot
- TCS105 Cleveland Jr. Cherry Bomb
- TCS106 Ladies' Night
- TCS107 A Brown Thanksgiving
- TCS108 From Bed to Worse
- TCS111 Love Rollercoaster
- TCS117 Gone with the Wind
- TCS118 Brotherly Love
- TCS119 Brown History Month
- TCS121 You're the Best Man, Cleveland Brown
- TCS201 Harder, Better, Faster, Browner
- TCS206 Fat and Wet
- TCS209 Beer Walk!
- TCS211 How Do You Solve a Problem Like Roberta?
- TCS222 Hot Cocoa Bang Bang (mentioned)
- TCS302 The Hurricane (mentioned)
- TCS303 Nightmare on Grace Street (mentioned)
- TCS307 Die Semi-Hard
- TCS310 Dancing with the Stools
- TCS311 Brown Magic
- TCS312 'Til Deaf
- TCS315 The Men in Me
- TCS318 B.M.O.C.
- TCS401 Escape From Goochland
- TCS402 Menace II Secret Society
- TCS404 Turkey Pot Die
- TCS405 A Vas Deferens Between Men & Women
- TCS408 Wide World of Cleveland Show
- TCS411 Brownsized
- TCS414 The Hangover Part Tubbs
- TCS419 Grave Danger (heard)