Last week, I wrote a piece ranking the central characters on It’s Always Sunny In Philadelphia from most to least evil. The conclusion that I came to was that Frank was the absolute worst, and Dennis was a very close second. Many of you disagreed with me, believing that Dennis was the most despicable of them all. While I still maintain that Frank is an inhuman monster, and being raised by Frank is a big reason why Dennis is so awful, I will concede that when it comes to pure evil, Dennis Reynolds is hard to beat. With that in mind, let’s take a look at his some of his absolute worst moments.

The time he tried to pick up girls at a pro-choice rally



This happened in just the second episode, and gave us a clear indication of what kind of show this was going to be. Dennis goes to a pro-choice rally, expecting to have an easy time meeting women. Instead, they figure out his intentions right away, and he is rejected by everyone he approaches. But the kicker comes at the end. When Dennis finds out that Mac has had far more success in his quest to hook-up with anti-abortion protester, he decides to jump the fence at the rally, and try his luck with the other side. He gets caught on the fence, and winds up getting screamed at by both groups. As good of an example of Dennis Reynolds getting what he deserved as you’ll ever find.

The time he offered to “frame-bang” someone….while she was sleeping!

As you’ll see multiple times on this list, Dennis’s views on sex are disturbing beyond anyone’s worst nightmares, and he seems to think “making love” to someone while they’re sleeping is completely okay and not a serious crime. Seriously, just watch this scene, and then take about 10 showers:

Because of the implication

This might be the most disturbing Dennis Reynolds moment ever. In this scene, he talks about buying a boat, taking it out to international waters, getting the women on the boat drunk, and planning to have sex with them by putting in a situation where they wouldn’t refuse “because of the implication.” Wow. Seriously, this is a deeply disturbing human being we are dealing with. If Dennis Reynolds were a real person, I’d swear he was the one hacked all those phones.

The time he revealed the secrets of The D.E.N.N.I.S. System

It’s hardly surprising that a man with so many disturbing views on women would have system them picking them up that even the creepiest pick-up artist would be a little skeeved-out by. Just in case you forgot the principles of The D.E.N.N.I.S. System, it goes like this:

Demonstrate value

Engage physically

Nurture dependence

Neglect emotionally

Inspire hope

Separate entirely

While it’s really not a hard system to remember (I didn’t even have to look it up to type it out), the rest of the gang still had an incredibly difficult time wrapping their heads around it. Which, honestly, was a huge relief for everyone else in Philadelphia.

The time he spent hours listening to audio of his sexual escapades

Okay, we’ve spent plenty of time exploring all the evil things Dennis Reynolds does and thinks. But let’s talk a bit about why he does these things: he’s a frightening combination of extremely narcissistic, and woefully insecure. And those characteristics came together memorably in the “Thunder Gun Express” episode. While everyone else is fighting each other to get to the movie, Dennis is in his car, listening to recordings of his encounters with the opposite sex. Mind you, he doesn’t just record the sex scenes — he records the entire date! In this case, he’s determined to disprove Mac’s assertion that he waits too long to make his move, then gradually discovers that Mac might have a point. Then, we find out the entire encounter was with a 16-year-old girl! So yeah, is one gross dude we’re dealing with.