Business Casual Superstar: Inspired by Sideshow Bob (Kelsey Grammer, “The Simpsons”) … Plus An Awesome FanMix!

YES. I did it. I put together an outfit (for the dudes) inspired by Sideshow Bob! Aren’t you proud of me? Basically, this is the culmination of an entire life’s work, you guys. I was born in anticipation of this moment, to share this outfit and this fabulous fanmix with you.

Seriously. It’s a rocking fanmix.

Now, Sideshow Bob normally wears prison blues. Or that blue suit with the red tie when he was busy being the mayor of Springfield. And also those normal street clothes of his, like when he was released from prison with one of those shock collar things to help figure out who was trying to kill Homer and then it turned out to be Frank Grimes, Jr. (Frank Grimes liked prostitutes.)


Yes, it’s had its fabulous years and it’s really crummy years. I don’t care. I find the Simpsons very, very comforting. They’re yellow people with big eyes that have been in my living room for like ten years.

(I wasn’t allowed to watch them when I was 13 because my mother thought they were scandalous and would ruin my morals and teach me to talk back to elders and stay out all night doing peyote and punch babies. Most of that happened anyway, but it wasn’t because of the Simpsons. Okay, it was because of the Simpsons. And this really bad batch of peyote I got this one time.)

Anyway, they’re comforting. No matter what is going on in my life, I can come home and turn on FOX or grab my DVDs and Marge will still have tall blue hair and go “hrrrm” all the time, and Lisa will still be a bleeding heart liberal know-it-all and Bart will still be causing trouble and Maggie will still be sucking on her pacifier and Homer will still be an idiot. They’ll never change.

Also, there are bright colors and funny noises and lots of movement and it really keeps my attention. :)

Anyway, Bob has a couple different outfits. But my favorite one is the one he wore in “The Italian Bob.” That’s a great episode. It makes my heart hurt for Bob, but still a great episode.

First, Mr. C. Montgomery Burns buys a Lamborgotti Fasterosa, and has to send an employee over to Italy to pick it up. That employee is, of course, Homer.


While traveling, Lisa wants everyone to think she’s Canadian. You know, because she’s SMART. Bart is not down with this plan.

Hahaha, Lisa not wanting anyone to know she’s American reminds me of the episode where the family is in London (THE SIMPSONS ARE GOING TO ENGLAND!) and Homer walks up to the guy at the hotel and is like, “AY. I’m an American! We saved your ass in Vietnam and shared our prostitutes with Hugh Grant, so give me some free maps and none of that dry British wit.” And the guy was like, “Wouldn’t dream of it, Sir.” WITH DRY BRITISH WIT.

I just want to add that the name of that episode was “The Regina Monologues,” and that’s cute.

The family gets to some little town in Tuscany and walks around and everything is perfect. But no one speaks English (except this little old lady who knows enough to let them know that in her language, “Kentucky” means “whore”). That is, except the mayor. (And, you know, that little old lady I just mentioned. But that’s not that dramatic.)






But yeah, Bob is the mayor.

Unlike in Springfield, though, this time Bob didn’t have to pack the ballot full of dead people and pets. He became mayor because his large feet made stamping grapes for the chianti a snap.

Turns out, Bob has a happy little family here and is doing quite well away from the Simpsons. He’s married to a gorgeous Italian bird and has a cute little baby that looks just like him. (Strong genes.)

At a town party, the baby dances with little Maggie and is just generally adorable with that wild crop of coarse ginger hair.

Oh, yeah, and the baby is crazy. As most babies are. (Like I said, strong genes.)

GROUP SHOT. 😀 I love this show so much.

Anyway, I loved Bob’s little outfit. His grey suit (which looked cream in other shots,, so I ended up going with cream instead when I made his outfit over) and his little tie and his huge shoes. Hahaha. You know what they say about a man with big feet.


He’s probably a clown.


What? What did you think I was going to say?!


That’s scandalous and you should all be ashamed.

Anyway, yeah, I loved Bob’s little outfit. But I just love Bob in general. So much so that I put together a lovely fanmix (seriously, I think it’s my favorite mix that I’ve ever made) about him. There are basically no Simpsons fanmixes out there, you guys. Can you believe it?! :-O This cannot stand.

Let’s get started. I made this for a challenge on LJ, and the art theme was ‘monochromatic’ so that explains that.

No One Who Speaks German Could Be An Evil Man: A Robert Underdunk Terwilliger FanMix

Track List and Info:

Make ‘Em Laugh: Joseph Gordon Levitt

This is from his SNL monologue, and I thought it worked well because you can hear the audience, and SNL cast members have little interludes, and it’s just very obvious that it’s a performance, much like the many many performances Sideshow Bob did with Krusty, where he was always the one being shot out of a cannon or punched in the face.

Why Can’t the English: Rex Harrison

Yep, from My Fair Lady. Sideshow Bob is a very articulate, well spoken, intelligent man, and he does not suffer fools (in grammar) gladly. Usually it is his downfall, like in that episode where he wanted to look up ‘hoisted with his own petard’ on the computer and then everything exploded.

Officer Krupke: West Side Story Cast

Sideshow Bob has had a billion run-ins with the law, and even though he’s always carted off to prison, it’s clear that law enforcement is bumbling and incompetent, and usually not the ones that successfully apprehend him. No, that would usually be Bart and Lisa.

What’s Opera, Doc: Bugs Bunny and Elmer Fudd

Guys. Bugs Bunny. Elmer Fudd. In costume. Wagner. SERIOUSLY. Is there anything better? It’s the entire six minute cartoon, with lots of operatic singing and awesomeness. And the “KILL THE WABBIT” bit totally captures the nature of Bob’s obsession with killing the boy.

Springtime for Hitler: The Producers (2005)

Remember when Bob became mayor? And he said that America’s conscience forced it to vote Democrat, but secretly, America wanted a politician that brutalized criminals and legislated morality and ruled them like a KING. Bahahahaha. How well does this song fit that? He really is Springfield’s little dictator but with hilariously terrible results.

What Kind of Fool Am I: Sammy Davis, Jr.

There had to be one song like this. It’s the rules, you guys. The rules of fanmixing. Bob hasn’t been very successful in love and has always been alone, and who knows, that may be part of the reason that he’s such a basketcase all the time and so fixated on killing Bart. After all, once he falls in love and gets married, he forgets all about the Simpsons.

On An Evening in Roma: Dean Martin

I was so happy for Bob when he married that gorgeous Italian bird and had an adorable little baby and became a fine, upstanding mayor and local celebrity. I kind of hated that the Simpsons came to town and Lisa derailed everything by getting drunk. (But why does Bob wear his prison jumpsuit under his normal suit? COME ON BOB.)

BONUS: For He Is An Englishman: HMS Pinafore: Kelsey Grammer

Kelsey Grammer has a fabulous voice, doesn’t he? It took me FOREVER to realize that was him. Like, embarrassingly wrong. This 30-second clip is probably my favorite one of Bob’s songs on the show.


See? Didn’t I tell you it was a great mix? I love it.

Now let’s move on to the clothes.

Izod Sweater in Peyote ………. $21.99
Tasso Elba Shirt ………. $14.99
Pants in Brown ………. $20
Berry Red Slim Tie ………. $8
Laughman Loafers ………. $31.49

Hah, a peyote mention! Nice. I love it when things come around like that. Also, the dude modeling the sweater is hot. (Something for the ladies. You’re welcome.)

Anyway, yes, creamy sweater, white dress shirt, brown pants, red tie, and brown loafers. Pretty simple. I opted for cream instead of grey (the screenshots go either way) because I liked the warmth of the color better, especially with the red tie.

Also, how epic is Sideshow Bob’s hair? I mean, really. Try to pull that off with your ‘do, too, gents. Then you’re set!