‘It’s Always Sunny in Philadelphia’: Best 14 Moments From 14 Seasons

As It’s Always Sunny in Philadelphia begins production on its 15th season, we’re look back on the zany sitcom’s most infamous shenanigans!

Connor Rose

AfterBuzz TV Producer, Host & Writer
Posted On: May 28th, 2021 7:24 pm pst

Maria Menounos
Keven Undergaro
AfterBuzz TV Founders

Founded by Emmy winning journalist Maria Menounos and Producer Keven Undergaro, AfterBuzz TV is the artist-friendly entertainment news platform that celebrates, discusses, interviews, promotes and reports on the widest range of stars, creators and content through video, audio and article publications.

‘It’s Always Sunny in Philadelphia,’ starring Rob McElhenney, Glenn Howerton, Charlie Day, Kaitlin Olson and Danny Devito has officially begun production on its 15th season. This upcoming season is especially notable as it will officially mark it as the longest running live-action sitcom in television history.

Since not much has been released about what season 15 has in store for the notorious Paddy’s Pub gang, we’re taking a look back at 14 of the show’s most memorable moments over their past 14 seasons!

1. The Mac and Charlie staredown – Season 8, Episode 9

One of the most iconic interactions in It’s Always Sunny in Philadelphia’s history, both for its hilarity and its meme-ability, is the obscenely-long stare between Paddy’s Pub owners Mac and Charlie, both dining at the same restaurant at different tables. The awkwardness is just perfect and speaks to very real interactions we all have when we see someone we know in public. A classic moment in an iconic episode.

2. Digging up Dennis and Dee’s mom – Season 8, Episode 6

In an episode centered around the notion that Frank, played by Danny Devito, is slowly losing his mind, the psychotic bar owner tricks his non-biological children, Dennis and Dee Reynolds, into digging up their dead mother’s grave on the false notion that she was actually alive and all that was in her grave would be money. Psychotic? Perhaps. Hilarious? Absolutely.

3. Mac and Charlie’s street justice – Season 13, Episode 5

When a gang of children steal Mac and Charlie’s new bikes, they decide to take matters into their own hands: attacking and beating up the young kids, possibly even killing one of them. The icing on the cake is that one of the children is the son of a man who stole Mac and Charlie’s bikes when they were kids, adding to their satisfaction as well as going full circle in a dark and violent way.

4. CharDee MacDennis – Season 7, Episode 7

I’m sure all fans of It’s Always Sunny in Philadelphia have wanted to play CharDee MacDennis. A game made by the Paddy’s Pub Gang to fuel friendly competition and promote the consumption of alcohol. The game consists of three rounds that sound each more painful, yet amusing, than the last. Anyone would be lucky to have a friend group that plays CharDee MacDennis together.

5. Frank captains a tour boat – Season 7, Episode 11

Some of It’s Always Sunny in Philadelphia’s funniest moments are when Frank Reynolds is given a platform to speak, best exemplified by his brief run as a boat captain and amateur tour guide. As the gang makes their way to see a blockbuster movie together, the world-renowned Thunder Gun Express, Frank is detoured by the opportunity to travel by boat and guide a group of curious tourists. The exchange makes for some of the funniest conversations in season 7 and is an excellent testament to the humor that Danny DeVito brings to the show.

6. Charlie the “Wildcard” – Season 4, Episode 2

Charlie Kelly, at his core, is a wildcard. With insane hijinks and psychotic antics, it’s perfectly clear why, when the Gang tells Charlie to be the “wildcard” during one of their get-rich schemes, things go off the rails real quick.

7. The Gang tries out for the Philadelphia Eagles – Season 3, Episode 2

It’s only human that the Gang, after watching the sports movie Invincible, would think that they could make it as athletes on level with the Philadelphia Eagles. As per usual, the Gang was wrong, leading to a breaking of ego and a variety of injuries. Plus, who can forget the first ever appearance of Green Man?

8. Dennis and Dee try to do their own botox – Season 4, Episode 10

As some of Paddy’s Pub’s token narcissists, it’s only natural that Dennis and Dee Reynolds’s path to ultimate perfection would lead them to botox, attempting to inject their own faces. However, things don’t go according to plan, leading to an eye injury that looked as painful as it probably felt.

9. The Pepe Silvia incident – Season 4, Episode 10

Another moment just as iconic and meme-able as the Mac and Charlie staredown is easily Charlie’s slope into insanity during his time as a mailroom employee. Burdened by carrying the responsibility of the mail room by himself, his mental breakdown in how determined he was to find out who Pepe Silvia was, is both hilarious and impressive. Say what you will, but Charlie’s got dedication.

10. The Gang buys a boat (feat. “The implication”) – Season 6, Episode 3

If there ever was a group of people that should never buy a boat, it’s the Paddy’s Pub gang. Their attempt to fix a run-down boat leads to dozens of hilarious antics, such as Frank’s refusal to throw things underhand. One of the most notorious moments, however, is Dennis’s speech about “implications” which slowly reveals to Mac just how sociopathic his best friend really is.

11. Mac and Dennis help Charlie date online – Season 5, Episode 5

A rare moment where Charlie isn’t hitting on the waitress at the Gang’s local coffee shop, Mac and Dennis feel the need to help their odd friend explore the world of online dating, leading to a number of iconic lines from Charlie Day’s infamous character. I get thinking people’s knees are a little weird, but who knew that ghouls could be considered an interest?

12. Ass Kickers United – Season 10, Episode 10

There’s something endearing about Mac’s enthusiasm for the lie that is Ass Kickers United, and it’s even funnier seeing the other members of the Paddy’s Pub gang use his devotion for their own ulterior motives. Honestly, I’m a little disappointed I never thought of making up a club like that to stop my friends from eating my Thin Mints.

13. The D.E.N.N.I.S. system – Season 5, Episode 10

Another perfect example of Dennis Reynolds’s narcissism is “The D.E.N.N.I.S. system,” a guide to casual dating that the potential serial killer enlightens his close friends with. In addition to being a hilarious bit, the D.E.N.N.I.S. system acts as a way of showing Dennis’s alarmingly sociopathic behavior. I personally think Dennis would make a great cameo in season 3 of You.

14. The Nightman Cometh – Season 4, Episode 13

Last but certainly not least is Charlie Kelly’s off-broadway musical, The Nightman Cometh, a testament to his obsession with the coffee shop waitress and his overall oddity. Honestly, I wish that this was a real musical that we could go and see. Who knows? Maybe Charlie Day can go out and actually write the show in its beautiful entirety.

What are some of your favorite moments from the show? Let us know in the comments!

About The Author:

Connor Rose is a screenwriting major at Loyola Marymount University. He is currently pursuing a career in the film industry as an actor and a screenwriter.

Founded by Emmy winning journalist Maria Menounos and Producer Keven Undergaro, artist-friendly AfterBuzz TV is the world’s largest digital broadcast network and pop culture news platform, producing post-game ‘after-shows’ for nearly all favorite TV shows, interviewing cast and showrunners and providing the widest video, audio and article coverage of shows, content and influencers than any entertainment news platforms in existence

“We don’t just celebrate and cover the top shows, content and stars, we celebrate and cover ALL the shows, content and stars.”

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