Sideshow Bob is an enchanting, complex character. So it's no wonder why he has all these tiny little references, tidbits, facts and stuff that are related to him in some way and/or contribute to his character. You might learn something. :)

Robert Underdunk Terwilliger, a.k.a. Sideshow Bob
Originally was a silent and nondescript background character. He did not become an evil genius until the "Krusty Gets Busted" episode at the end of the first season.

His first appearance was February 25, 1990, "The Telltale Head".
The script originally called for James Earl Jones to voice Sideshow Bob, but the producers' final decision was Kelsey Grammer.

Originally looked completely different than he does now. In "The Telltale Head", his design was very simple: his famous spiked hair was a simple round afro, his nose was also more rounded, eyes very close together and not nearly as expressive as they are now, and he looked generally heavier than his more slender form we recognize now. It was director Brad Bird's idea to redesign Bob to better fit Kelsey Grammer's voicing for him. Before "Krusty Gets Busted" aired, the animators tried to re-animate Bob's brief appearance in "The Telltale Head", but there wasn't enough time.

Another early concept was that in every episode in which Sideshow Bob appears, there would be a recap of every evil deed he's done so far. This was dropped after "Brother From Another Series" because the list was getting too long for recapping already.

He is a classically trained actor, former sidekick to Krusty (whom he hates) and multiple felon (including four attempted murders, one electoral fraud and one plot to abolish television). Currently residing in Springfield Penitentiary, where he mostly dreams of revenge and hatching many evil schemes, and once staged a prison production of "Evita."

He ranked #2 in's 2006 list of the "Top 25 Simpsons Peripheral Characters", described as: "a man of contradictions; his goofy appearance, complete with palm tree like hair, doesn't seem to match up to the well spoken and even musically talented maniac."

He's the #66th greatest villain of all time, as decided by Wizard Magazine.

A memorable line is "Attempted murder. Now, honestly, what is that? Do they give the Nobel Prize for attempted chemistry?"

Movie/TV references

his middle name is his mother's maiden name (Underdunk)
shares personality characteristics with Frasier Crane (Kelsey Grammer's other most famous role); has been described as "Frasier pickled in arsenic" (Ken Tucker)
is an ex-con, like Robert Mitchum/Robert De Niro [Cape Fear; episode title and plot of "Cape Feare" [9F22] is a take-off of this film]
his uniquely dignified comic style is similar to Buster Keaton's.
possibly inspired by, and named after, the evil Dr. Terwilliker in "The 5000 Fingers of Dr. T", a 1953 movie about a man who controls 500 small boys by teaching them to play the piano.
brother Cecil is Kelsey Grammer's television brother Niles as played by David Hyde Pierce in "Frasier".
father Dr. Robert Terwilliger, Sr., is voiced by John Mahoney, who plays Martin Crane- father of Frasier and Niles.
according to Kelsey Grammer, Sideshow Bob's voice is based on actor Ellis Rabb's.
Ellis Rabb played a character in the 1979 movie "A Life in the Theater". The character was named Robert!
episode title "Sideshow Bob Roberts" is from the movie "Bob Roberts". The movie is pointed political satire about an unethical Republican politician.
episode title "Sideshow Bob's Last Gleaming" reflects "Twilight's Last Gleaming" - about a renegade general who escapes military prison and takes over a silo, threatening a war 'til he finds details of some certain secret.
episode title "Brother from Another Series" parodies a movie "Brother from Another Planet" about an alien slave that escaped to Earth.
episode title "Day of the Jackanapes", yet another parody of a movie title. "Day of the Jackal", about a professional assassin plotting to kill the President of France. Notice a pattern already?
episode title "The Great Louse Detective" parodies "The Great Mouse Detective", an old Walt Disney animated film.
episode title "The Italian Bob" is a take-off of the movie "The Italian Job".
Kelsey Grammer recorded lines for Sideshow Bob in "The Simpsons Movie", but his scenes were cut (presumably for time).

By Any Other Name:
Where did Sideshow Bob Terwilliger's name come from?

Terwilliger is a boulevard in SW Portland.
Terwilliger could be named after L.L. Terwilliger, the first principal of a public school in Portland; the school was at 6th and SW Morrison, which is where Pioneer Courthouse Square is today.
Terwilliger could be named after "Sergeant Terwilliger" and "Mrs. Onderdonk" from the pilot episode of a TV show called "Hunter".

That's about all in these categories. What, there's no more here! Go on!

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disclaimer: "The Simpsons", 'Sideshow Bob' and related characters Matt Groening and FOX. "Evil Laughter" is a part of, Janna Correa.