13 Dark Humor Jokes and Moments from Andy Daly
It’s hard to find a comedian with a more disturbingly chipper voice than Andy Daly — and he’s made a multi-decade comedy career because of it. Daly’s dark, disturbing wit plays in perfect contrast with his naturally bright and vibrant line delivery. If you have a role of a nebbish “beta male” with a sinister streak, he’s the first person you seek out.
Click right here to get the best of Cracked sent to your inbox.
For more than 30 years, Daly has been able to forge several lighthearted, yet deranged characters that brought us big laughs alongside the depravity lurking beneath the surface. Which is what led us to collect some of the best dark humor jokes and moments from Daly’s deeply diverse career...
As a Terrified Bob’s Big Boy Statue
Daly revealed the dark side of the cheerful fast-food mascot, who armed himself to the teeth after hearing that Confederate statues were being torn down. Frankly, he should be torn down for creating the song “Despacito” alone.
As Krombopulous Michael on ‘Rick and Morty’
Playing into his affability, Daly provides an uncanny cheerfulness to his role as an alien assassin who frequently buys weapons from Rick. He just really loves killing.
Andy Daly as Dalton Wilcox
Dalton Wilcox is known for killing people he believes are monsters, but also the dark loneliness that a cowboy can experience and the desperation that leads to, well, unique sexual adventure.
As Terrence Cutler in ‘Eastbound & Down’
Daly’s deficiencies in comparison to the peak specimen that is Kenny Powers inspired desperate moments in the series, such as trying to chloroform and kill Kenny after being in the woods.
Getting Trapped in a Marriage on ‘MADtv’
Early in his career, Daly was a cast member on MADtv and was featured in several sketches, including one in which a married couple watches their wedding video, after which things take a real turn.
Asking the Questions That Everyone Is Really Thinking
As Johnathan P. Scroat, Superintendent of Public Schools
In this MadTV parody of old moralistic educational films, Daly renounces rock and roll while revealing the ridiculous yet sinister fallout of trying to live like a Norman Rockwell painting.
As Reed Newport, 1980s Game-Show Host
Daly had a goofy time on Conan as a talk-show host/stroke victim whose show was canceled 30 years ago and hears the voice of his mother.
UCB Improv: Trying Crack During a Family Trip
Considered one of the country’s top improvisers, Daly is able to use his quick wit to make any bit take a turn for the darker, just like this scene in which he plays an unlikely crack customer.
As Chip Gardner, the Satanic Candidate Running for Mayor of Hollywood
Gardner is a game-show host vying to become honorary Mayor of Hollywood that hosted a series of grisly game shows and thanks the Dark Lord Satan for rescuing him from despair after his face got run over by a Jeep.
As Dr. Crawford on ‘Silicon Valley’
Daly would occasionally pop up on the HBO comedy as a physician who shared way too much about his patients’ medical history with Richard, especially the fallout of one’s suicide attempt.
As Don Dimello, Theatrical Director
Touted as probably the vilest of Daly’s characters, Dimello was Daly at his most skeevy and sinister. This popular Comedy Bang! Bang! character was known for his shady theatrical productions and horrifying treatment of young actresses.
Pancakes, Divorce, Pancakes from ‘Review’
The crowning achievement of the criminally underrated series Review, the episode “Pancakes, Divorce, Pancakes” is a masterpiece of dark comedy. As only he can, Daly turned something as ridiculous as eating 30 pancakes into a somber tale of despair and ennui.
