Ranking Every Season Of It's Always Sunny In Philadelphia From Worst To Best
8. Season 6
Thanks to the real life pregnancy of Kaitlin Olson, this season sees Dee become pregnant. Dennis also falls into a marriage and subsequent divorce to Maureen Ponderosa. These two things make up for an odd season that sees a common storyline tie all the episodes of one season together, which we would actually see in the next season again with fat Mac. Season 2 did have the addition of Frank as Dennis and Dee's dad overarching the season, but it never felt as significant as Dee's pregnancy in Season 6 or Mac's obesity in Season 7.
"The Gang Buys a Boat" sees the gang, well, buy a boat and it's the best look into the sadistic mind of Dennis Reynolds since "The D.E.N.N.I.S. System" a season prior. It goes over his love of the open water, because of the implication.
Other highlights of the season include "Mac and Charlie: White Trash," "Mac's Big Break" and "Who Got Dee Pregnant?" As well as the cameo of Jason Sudeikis and Dave Foley in "The Gang Gets a New Member." Season 6 is about as strong as they come when it comes to reoccurring characters and guest stars joining the mix.
Among the highlights are a few duds like "Mac's Mom Burns Her House Down" and "Dee Reynolds: Shaping America's Youth." There's also an hour long Christmas special which, while technically counted as part of Season 6, was released a year prior on DVD and was very obviously filmed prior as it's not in HD like Season 6, which was the first season to do so. That being said though, Charlie confronting Santa for banging his mom is one of the funniest Sunny moments ever.