7. Brian Sings And Swings
Music is a huge part of Family Guy, helped in large part by Seth MacFarlane's legit crooning credentials (he's cut a good side-career as an opera singer.) As Brian is voiced pretty much exactly as MacFarlane speaks, the character benefits from the show creator's baritone to sing with the likes of Frank Sinatra Jr. In Brian Sings And Swings, we see him do just that after becoming depressed due to the injuries caused by Peter running him over: he resorts to moping and drinking. This is short-lived, however as he meets Frank Sinatra Jr. and begins to tour with him, which changes his outlook on life but does little to curb his alcoholism. In the drunken aftermath of one show he loses Stewie who is subsequently mauled by a deer. Peter is furious with Brian and in the ensuing confrontation tells him to stop performing with Sinatra. This leads to an out of character outburst from Brian, who bites Peter causing a rift between the best friends. It's flaws like this that make Brian so compelling and after sinking lower and drinking wine in the gutter, he gets his happy ending, performing with Stewie and Sinatra to close the episode. Brian's journey through depression and remorse is of course told with a comedic leaning, but there is a lot of heart to the episode, he learns that there are things out of his control and takes ownership of his mistakes.