David Boat (fantasized bear-human hybrid appearances only)
Rupert is Stewie Griffin's teddy bear. Though inanimate, Rupert has become his personal confidant and best friend. Stewie confides all his secrets and machinations in Rupert, and often gets upset when Rupert does not respond. Rupert has also been known to double as a pistol when needed.
Rupert is first seen as a brown teddy bear, but in later episodes he appears more orange.
Rupert has been damaged several times. The first time in a flashback in "Stu & Stewie's Excellent Adventure", Stewie argued with Brian about the economy and Brian decided to eat one of Rupert's legs; Stewie got the leg back after a while. The second time involved encountering an unfamiliar Rottweiler dog in "Stewie Loves Lois". Rupert was torn to shreds but was later fixed by Stewie's mother Lois. It also seems that when Rupert doubles as a gun, his head needs to be ripped off, and Lois seems to fix that by the next scene in the episode. Also, in "A Very Special Family Guy Freakin' Christmas", Stewie tears Rupert in two, after waking up from a Santa Claus-themed nightmare. In "Killer Queen", Stewie shoots Rupert in the head with a gun rather than risk letting him die a worse death when he sees the cover of a Queen album. In "Lois Comes Out of Her Shell", Sheldon tears Rupert's head off and leaves it in a box for Stewie to find.
In "The Man with Two Brians", he is humped by New Brian for two hours. Stewie then is then shown dragging a body in to the garbage, later revealed to be New Brian. At the end of the episode Stewie is shown crying in the shower and washing Rupert in despair, constantly reassuring him that it wasn't his fault. In "Chick Cancer", when Stewie married Olivia Fuller, he had Rupert officiate the ceremony.
"8 Simple Rules for Buying My Teenage Daughter" had the creation of "Stewpert", a being where Stewie and Rupert were fused together after Stewie activated his teleportation device before he realized Rupert was inside, in reference to Brundlefly of The Fly.
Stewie had several times referred to him as gay. Stewie accused Rupert of choosing to watch the boys in "Road to Rhode Island" as opposed to watching their bags as Stewie has told him to, much to Stewie's chagrin. Stewie has also imagined Rupert as a muscular, human male a few times, including in "Road to the North Pole", where he builds a buff Rupert snowman in the opening credit sequence. However, Rupert retains his Teddy Bear head. During these dreams, Rupert is voiced by David Boat. In a DVD exclusive scene in "Excellence in Broadcasting", Stewie explores the experience of masturbating and in his fantasy buff Rupert makes out with an equally buff Brian while Stewie is tied to the bed.
Rupert is recalled by the toy company in "Total Recall" and Stewie launches an all-out effort to recover him before he is destroyed.
In the courtroom scene in "The Simpsons Guy", Stewie is seen holding Rupert next to Mr. Burns who is holding his teddy bear Bobo.
- FG107 "Brian: Portrait of a Dog"
- FG201 "Peter, Peter, Caviar Eater"
- FG204 "Brian in Love"
- FG215 "Dammit Janet!"
- FG309 "Mr. Saturday Knight"
- FG311 "Emission Impossible"
- FG316 "A Very Special Family Guy Freakin' Christmas"
- FG408 "8 Simple Rules for Buying My Teenage Daughter"
- FG409 "Breaking Out is Hard to Do"
- FG410 "Model Misbehavior"
- FG428 "Stewie B. Goode"
- FG430 "Stu & Stewie's Excellent Adventure"
- FG501 "Stewie Loves Lois"
- FG506 "Prick Up Your Ears"
- FG507 "Chick Cancer"
- FG509 "Road to Rupert"
- FG510 "Peter's Two Dads"
- FG604 "Stewie Kills Lois"
- FG605 "Lois Kills Stewie"
- FG704 "Baby Not On Board"
- FG705 "The Man with Two Brians"
- FG713 "Stew-Roids"
- FG808 "Dog Gone"
- FG810 "Big Man on Hippocampus"
- FG811 "Dial Meg for Murder"
- FG813 "Go, Stewie, Go!"
- FG815 "Brian Griffin's House of Payne"
- FG902 "Excellence in Broadcasting" [DVD exclusive)
- FG904 "Halloween on Spooner Street"
- FG906 "Brian Writes a Bestseller"
- FG907 "Road to the North Pole"
- FG909 "And I'm Joyce Kinney"
- FG913 "Trading Places"
- FG915 "Brothers & Sisters"
- FG1002 "Seahorse Seashell Party"
- FG1004 "Stewie Goes for a Drive"
- FG1005 "Back to the Pilot"
- FG1016 "Killer Queen"
- FG1019 "Mr. and Mrs. Stewie"
- FG1022 "Family Guy Viewer Mail No. 2"
- FG1103 "The Old Man and the Big 'C'"
- FG1105 "Joe's Revenge"
- FG1106 "Lois Comes Out of Her Shell"
- FG1107 "Friends Without Benefits"
- FG1110 "Brian's Play"
- FG1111 "The Giggity Wife"
- FG1112 "Valentine's Day in Quahog"
- FG1113 "Chris Cross"
- FG1117 "Bigfat"
- FG1118 "Total Recall"
- FG1121 "Roads to Vegas"
- FG1203 "Quagmire's Quagmire"
- FG1205 "Boopa-Dee Bappa-Dee"
- FG1206 "Life of Brian"
- FG1207 "Into Harmony's Way"
- FG1212 "Mom's the Word"
- FG1216 "Herpe, the Love Sore"
- FG1216 "Meg Stinks!"
- FG1221 "Chap Stewie"
- FG1301 "The Simpsons Guy"
- FG1303 "Baking Bad"