While Halloween episodes can verge on cliche, “Sunny” takes on a real-life scare: pregnancy. Dee finds out she’s pregnant and isn’t sure who the father is, leading the guys to backtrack to see if it could be one of theirs. This makes for wild flashbacks and great use of recurring characters to write in Kaitlin Olson’s real-life pregnancy.
2. “The Nightman Cometh”
Airdate: Nov. 20, 2008
Not the only musical episode, but certainly a memorable one: Charlie builds on his song “The Nightman” to write a musical involving the gang to woo the waitress that he’s obsessed with (Mary Elizabeth Ellis who is married to Charlie Day in real life). The disastrous onscreen production nevertheless led to the cast giving live performances of the act across the country.
3. “The Gang Gives Frank an Intervention”
Airdate: Oct. 8, 2009
Sometimes, it takes an innocent bystander to show just how screwed up the gang is. In this episode, that takes the form of an unsuspecting therapist who shows up for Frank’s intervention (that the gang throws him because he’s no longer fun to drink with), one that leads to more superfluous interventions.
4. “Paddy’s Pub: Home of the Original Kitten Mittens”
Airdate: Nov. 5, 2009
Though the gang can sometimes (well, most of the time) get pretty dark, the highlight of this episode involved an adorable product called Kitten Mittens — or “Mittons,” per Charlie’s illiteracy. Brought on by an incoming merchandise convention, Charlie produces a highly gif-able commercial for mittens to quiet cats’ paws.
5. “CharDee MacDennis: The Games of Games”
Airdate: Oct. 27, 2011
In a prime example of a bottle episode, the gang introduced “CharDee MacDennis,” a game based on three stages: mind, spirit and body. The utterly ridiculous game ultimately amounted to ruthless verbal battery and allowed viewers to see the horror of the borderline sociopathic Reynolds twins.