Sideshow Bob is probably the greatest guest character that The Simpsons ever created, and the casting of Kelsey Grammer is the biggest part of what makes this character so enduring.  His voice, so rich and lyrical, brings Bob to life time and time again.  His character appeared in the very first season and has gone on to appear in eleven more episodes…well…twelve actually but one of those wasn’t really a  proper Bob episode…so we wont count that one.

As we approach the premiere of the 25th season of The Simpsons, I thought it would be fun to go through all those classic Sideshow Bob episodes…and rank the crap outta them!  So here we go, we’ll start from the worst and work our way up to…the very best Sideshow Bob episode ever.

11. The Italian Bob

Sideshow Bob: We are here to honor my old friends, the Simpsons. Tomorrow they return to America, taking with them my gratitude, my friendship, and my heartfelt wish that they never return.

Why do we want to see a Sideshow Bob who doesn’t want to take revenge on the Simpsons?  That’s right, we don’t.  The Simpsons discover that Sideshow Bob is secretly mayor of a small Italian town and…well that’s about it.  Not a lot of laughs, not a lot of fun, but thankfully Bob’s homicidal ways are restored by the episodes conclusion…although now he’s saddled with a wife and kid.

10. The Great Louse Detective

Sideshow Bob: Homer, how can one man have so many enemies? 
Homer: I’m a people person… who drinks.

To be honest…this episode probably doesn’t deserve to to be so far down the list, but it’s down here because it spits on one of my favourite episodes, Homer’s Enemy.  They bring back the son of Frank Grimes (apparently he liked hookers) who happens to look and sound just like his father and sets out to kill Homer in revenge.  Sideshow Bob helps the Simpsons uncover the culprit and as a reward is promptly set back to prison.

9. Funeral for a Fiend

Sideshow Bob: “Before you die, perhaps you’d like to know how I engineered my ultimate revenge.” 
 Homer:” I’d like to know if Wes Doobner is aware of what you’re doing in his restaurant!” 
 Sideshow Bob: “I’m Wes Doobner!” 
 Homer: “Mr. Doobner, I have a complaint: I work hard and when I go out with my family I expect a certain level of basic–” 
 Sideshow Bob: “Shut up!”

Although this episode does have several points going for it, namely John Mahoney and David Hyde Pierce playing Bob’s father and brother respectively, it ultimately falls flat.  Bob’s ploy to frame the Simpsons for his “death” never really finds its footing and ends up being more boring than it should be.

8. Day of the Jackanapes

Sideshow Bob: Rakes, my old archenemy! 
Bart: I thought I was your archenemy! 
Sideshow Bob: I have a life outside of you, Bart

After hearing that Krusty has taped over all the old episodes of The Krusty the Clown Show in which Bob appeared (blank tape was $3.99!) Sideshow Bob brainwashes Bart to kill Krusty.  The episode isn’t bad, although it suffers from being in the era directly after the golden age of The Simpsons.  The cliches of that period, random tangents and unbelievable plot points are all here.

7. Krusty Gets Busted

Sideshow Bob: Today’s show promises to be a marvelous celebration of the human spirit…but first I regret to say I see a youngster who looks troubled.  What’s your name young man?
Bart: Bart Simpson sir.
Sideshow Bob: Hrm, well perhaps we can shed some light on your problem in a new segment exploring pre-adolescent turmoil.  I call it…choices.

The very first Sideshow Bob episode is a little rough around the edges, but all the seeds are there.  The conniving frame-up plot, the maniacal laugh, Bob even sings his first song.  You could say the same for the whole first season of the show really, it’s rough but it’s definitely The Simpsons.

6. The Bob Next Door

Sideshow Bob: I can stand in one state, fire a gun in the second state, the bullet will travel through the third, hitting you in the fourth, so you’ll fall down dead in the fifth! No single act is against any law, but their sum total is the greatest murder since Snape killed Dumbledore! 
Bart: Oh, I haven’t gotten to that part yet! 
Sideshow Bob: It’s a four year old book. 
Bart: I’m a slow reader. 
Sideshow Bob: A fitting epitaph.

I was surprised that this episode ended up so high on the list considering its status as the most recent Sideshow Bob episode.  Why do I like it?  Well, after the previous few lackluster episodes this one felt refreshing because it offered a original story which returns Sideshow Bob to his menacing Bart killing roots.  The method in which he escapes prison and how he intends to kill Bart are rather clever and make for an all around enjoyable episode that brings a bit of the old style back.

5. Brother From Another Series

Sideshow Bob: “Just the thought of all that raw, surging power makes me wonder why the hell I should care.”
Cecil: “Because, you’ll be supervising the construction crew.” 
Sideshow Bob: “Oh great, whenever a woman walks by, I suppose it will be my job to lead the hooting  ‘Oh yeah! Shake it, madam! Capital knockers!’ “

Sideshow Bob doesn’t try to kill anyone in this episode, nor does he hatch any evil schemes.  Unlike the other episodes in which that happens…this one works.  The reason it works is thanks in large part to the wonderful wordplay between Bob and his brother Cecil, played brilliantly by David Hyde Pierce.  David is obviously no stranger to playing the brother to Kelsey Grammer, as he played Niles Crane on Frasier.  Of course that means we get several funny Frasier references through the show.  I can’t really picture this episode working without him, they’re such a perfect pair.

4. Sideshow Bob Roberts

Bart: We want the truth!
Sideshow Bob: You want the truth!? You can’t handle the truth! No truth-handler you are! I deride your truth-handling abilities!

The Simpsons taking on politics always makes for a good show, throw in Sideshow Bob and you have a great show.

3.Sideshow Bob’s Last Gleaming

Sideshow Bob: Well, if it isn’t my arch-nemesis, Bart Simpson. And his sister, Lisa, to whom I’m fairly indifferent.

One of the more…outrageous Sideshow Bob episodes (come on! He tries to detonate a nuclear device!) has Bob demanding the end of all television in Springfield.  It’s absolutely over the top from beginning to end as Bob actually wins…briefly, before he’s foiled by Bart, Lisa, and a clueless Krusty.

2. Black Widower

Sideshow Bob: Selma, would you mind if I did something bold and shocking in front of your family?
Selma: All right, but no tongues.
Sideshow Bob: Although kissing you would be like kissing some divine ashtray, that’s not what I had in mind. Selma, will you marry me?
Bart: Don’t be a fool, Aunt Selma. That man is scum.
Selma: Then call me Mrs. Scum.

Bob returns for the second time in an episode that’s a vast improvement over its predecessor.  Bob cons Selma into marrying him and Bart is the only one who realizes something is up.  This episode came around in the third season and during that interval between this episode and Krusty Gets Busted, the show had time to find its legs and strengthen its comedic sensibilities.

1. Cape Feare

Sideshow Bob: Bart Simpson, that mischievous little scamp that twice sent me to that dank, urine soaked hellhole. 
Parole Officer: Uh…We object to the term: “urine soaked hellhole,” when you could of used: “peepee soaked heckhole.” 
Sideshow Bob: Cheerfully withdrawn.

To be honest…there’s not a lot to say about this episode.  Not only is it the perfect Sideshow Bob episode, but it’s also the perfect Simpsons episode.  It has heart and most importantly, the laughs come hard and fast.  I’ve watched this episode a hundred times at least and I still laugh out loud every time.  I can’t think of any greater praise.

What about you folks?  Which Sideshow Bob episodes are your favourites?  You can even rank them for yourself in the comments!