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From Death Lives we learn he and Peter meet when Cleveland picked him up hitchhiking sometime during their teens early twenties & according to Meet the Quagmires they worked at the Country Club where Peter and Lois first met.

Cleveland owns and operates the Quahog Deli.
He was once married to Loretta but after she slept with Glen and he didn't react strong enough for her she left him and took Cleveland Jr. with her.

As of September 2009, Cleveland will no longer be on Family Guy because Mike Henry has taken Cleveland and (w/ the help of Seth MacFarland of course) created his own show.
The premise of the show is, Cleveland leaves Quahog and w/ Cleveland Jr. in tow takes a cross country vacation. He happens to pass through Stoolbend VA, Cleveland's home town and decides to stop.

He rekindles his romance with his high school girlfriend, Donna and they get married.
He moves Cleveland Jr. into her home with her 2 kids.

Herbert is an old man that was first introduced in “To Love and Die in Dixie”. He was a customer on Chris' paper delivery route. He has a dog named Jesse although Jesse hasn't been seen since “Bill and Peter's Bogus Journey”

It is assumed he also a registered sex offender because of his comments to the mayoral candidate Lois in “It Takes a Village Idiot, and I Married One”

It is also assumed Herbert is a homosexual because in “Dixie” we learned very early he was attracted Chris calling him “muscly arm” and trying to get him in his house by bribing him with Popsicles.

Chris seemed oblivious to Herbert's attentions until the episode “Play It Again, Brian” when Chris finally asked him if he's a pedophile.
However, his interests have turned away from Chris in recent episodes.
In “Movin' Out (Brian's Song)” he seemed very excited that Stewie took over Chris' paper route and in “The Tan Aquatic with Steve Zissou” Herbert was using another paperboy entirely named Kyle.

We learn in “Padre De Familia” he is a war veteran and received a purple heart.

Even though Mike Henry has left Family Guy, it was stated in an episode commentary on Volume 7 his others characters will remain in Quahog so Herbert should still make appearances from time to time.

After losing his Quahog home to Loretta in the divorce and finally getting fed up with Peter Griffin's shenanigans, Cleveland packs up his belongings & with his 14 year old son Cleveland Junior in tow, decides to move to California to pursue his dreams of being a minor league scout for a professional baseball organization.

He winds up traveling through his hometown of Stoolbend, Virginia, where by chance he meets his high school crush, Donna.
He soon meets and hits it off with Donna's neighbors, Holt, Lester & Tim and also discovers to his great disappointment, Donna's ex-husband Robert is still in the picture.

Rallo is Donna's 5 year old son and Cleveland's stepson.
Rallo is quick with the one liners & has a thing for the ladies.

He was kicked out of school for pulling down his teacher's pants, but with Cleveland's help, was admitted back into school and was taught the proper way to check out the girls.

Rallo was first introduced in the “Pilot” episode.