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The Simpsons: 10 Funny "Sideshow Bob Rakes" Memes That Make Us Laugh

The mark of a truly great show is its ability to create secondary characters that are even more fun to watch than the main ones. The Simpsons has succeeded in that regard, and one its finest creations is Sideshow Bob, the villain with the mellifluous voice. In one of the series’ most iconic scenes, Sideshow Bob finds himself thwarted by a series of rakes, which he inexplicably keeps stepping on (much to his annoyance).

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It’s one of those moments that’s gone down in television history and, as often happens with such scenes, it’s become the stuff of which hilarious memes are made.

10 The Best Of All Worlds

Despite his best efforts to do away with Bart (and sometimes his sister, Lisa), Sideshow Bob always finds himself apprehended by the police and taken away. The brilliance of this meme is the way in which it seamlessly blends Chief Wiggum, Troy McClure, and the rake.

It’s more than a little ridiculous, of course, but very much in keeping with Bob’s many plans, all of which are, it must be said, doomed from the very beginning because of how complicated they are.

9 The Horror!

Let’s be honest. It takes quite a lot to scare Sideshow Bob. This is a man, after all, who really hasn’t shied away from trying to murder a kid (and, in at least one instance, succeeded in doing so).

However, as this meme illustrates, he really has some good reasons to be afraid of rakes, given how troublesome they have been for him and his grand designs to do away with Bart. One can’t blame him for being a little prone to terror.

8 Computer + Rake = Evil

Despite the fact that technology is supposed to make life simple for people, in reality, it often makes things more complicated and difficult, making one wonder whether it’s even worth keeping around.

It stands to reason that this would be even more true for Sideshow Bob, who also seems to have a propensity for attracting difficulties. This meme deftly brings together the perils of technology and the even more perilous creation of mankind: the rake.

7 The Best-Laid Plans Go Oft A-Rake

A lot of people had grand ambitions for 2020. This was supposed to be a great year, after all, but the pandemic (along with a host of other issues) have ensured that this is a year that most people would almost certainly rather forget.

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Given this fact, and given how flexible the rakes meme has been, it’s really not surprising that someone would create a meme using the rake to show how many well-laid plans that people have made have been upended by the various crises in the world.

6 Gotta Love Kelsey

One of the things that makes Sideshow Bob such a great character is, of course, the fact that he’s voiced by none other than Kelsey Grammer, who gives the character a smooth sophistication that makes him distinct from many other characters in the show’s universe.

One can’t blame the characters in this funny meme for wanting to see Sideshow Bob step on a few rakes, since it’s such a hilarious and enduring part of the series’ legacy.

5 There’s Something Sinister Here

It’s bad enough that Bob had the incident with the rake way back in the day, but it seems like he’s never going to be able to get away from it. In this meme, he’s being pursued by the rake.

Even though Bob would no doubt be horrified, to the audience, it’s more than a little hilarious (and very fitting) to see Bob pursued by an inanimate object in much the same way that he has made a veritable profession out of pursuing Bart.

4 Absolutely Horrifying

Sometimes, the internet comes up with a meme that manages to be both hilarious and horrifying at the same time. There seems to be something about The Simpsons in particular that lends itself to this sort of meme, as one can see with this example, in which Homer’s face has meshed with the ubiquitous rake.

It is hilarious, but there’s also something more than a little creepy about it as well, and one can’t blame Bob for being terrified.

3 Bob Just Can’t Win

In keeping with the trend of using the rake and Bob to comment on the damage caused by the entire year of 2020, this meme shows what might be lost this fall.

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Not only will Bob’s efforts to bring about the death of Bart Simpson most likely come to nothing (as they always will), but it’s entirely possible that Halloween, as most people have come to know and celebrate it, might have to be changed to accommodate the perils posed by the pandemic.

2 Is There A Life Outside Bart?

There’s no question that, for Bob, the rake is one of his dreaded archenemies. But, then again, so is Bart, who has been responsible for so many of his plans going awry.

The hilarity of this meme is that it highlights that, for Bob, Bart and the rake exist in a kind of equilibrium, and it’s pretty hilarious to think that Bart might be jealous of the fact that an inanimate object has taken his exalted place in Bob’s affections.

1 A Mood, Indeed

Almost everyone has had one of those days (or weeks, or months, or years), where everything they do seems to go awry. That’s precisely what makes the incident with Bob and the rake such a flexible source for meme culture.

With the simple word “mood,” this meme manages to capture the sense of despair that many people experience when faced with the fact that all of their efforts just seem to make things infinitely worse than they were to begin with.

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