What was Sideshow Bob's first episode?

Answer 1

• Episode - "The Telltale Head"

• Episode - "Krusty Gets Busted"

• Episode - "Bart Gets an "F""

• Episode - "Stark Raving Dad"

• Episode - "Bart the Murderer"

• Episode - "Black Widower"

• Episode - "Lisa's First Word"

• Episode - "Cape Feare"

• Episode - "Another Simpsons Clip Show"

• Episode - "Sideshow Bob Roberts"

• THOH - "Treehouse of Horror V" (picture)
• Episode - "Sideshow Bob's Last Gleaming"

• Episode - "Bart the Fink" (mentioned)

• Episode - "The Day the Violence Died" (mentioned)

• Episode - "Brother from Another Series"

• Episode - "Behind the Laughter" (picture)

• Episode - "Pokey Mom"

• Episode - "Worst Episode Ever" (picture)

• Episode - "Day of the Jackanapes"

• Episode - "Large Marge" (promotional image only)

• Episode - "The Great Louse Detective"

• Episode - "Mr. Spritz Goes to Washington" (picture)

• Episode - "Mobile Homer" (couch gag)

• Episode - "The Italian Bob"

• Episode - "The Mook, the Chef, the Wife and Her Homer" (promotional image only)

• Episode - "You Kent Always Say What You Want" (picture)

• Episode - "Funeral for a Fiend"

• Episode - "Eternal Moonshine of the Simpson Mind" (gravestone)

• Special - The Simpsons Ride
• Episode - "Sex, Pies and Idiot Scrapes"

• Episode - "How the Test Was Won" (couch gag)

• Episode - "Wedding for Disaster"

• Episode - "Coming to Homerica" (couch gag)

• Episode - "Oh Brother, Where Bart Thou?"

• Episode - "American History X-cellent"

• Episode - "Chief of Hearts" (photo over end credits)

• Episode - "The Bob Next Door"

• THOH - "Treehouse of Horror XXII" (picture)
• Episode - "Holidays of Future Passed" (outline on floor)

• Episode - "Moe Goes From Rags to Riches" (couch gag)

• Episode - "At Long Last Leave"

• Episode - "Moonshine River"

• Episode - "Gone Abie Gone" (image on Poker site)

• Episode - "A Tree Grows in Springfield" (title screen gag, "Logomania" - picture)

• Episode - "Dark Knight Court"

• Episode - "Homerland"

• THOH - "Treehouse of Horror XXIV"
• Episode - "The Man Who Grew Too Much"

• Episode - "Clown in the Dumps"

• Episode - "Blazed and Confused"

• Episode - "I Won't Be Home For Christmas"

• Episode - "Peeping Mom"

Answer 2

His first appearance is The Telltale Head but his first speaking role is Krusty Gets Busted.