Chippy, a grotesque hairy baby-like...thing, that appears Once per Episode, often popping up suddenly, shrieking at the camera in either terror or agony. Making this worse is that no one on the show seems at all disturbed by Chippy and even regard it with affection.
Also, the episode "Forest" reveals that there are ADULT Chippies. And they are very territorial, hostile, and violent. Sweet dreams.
David Liebe Hart and his puppets. He does terrible ventriloquist acts with astonishingly ugly dummies and sings very badly, often about aliens, and it's very uncomfortable to watch. What really makes this creepy though is that Hart isn't acting—that really is him. The real Tim & Eric had Hart join them in the audio commentary once, and even they seemed at a loss for words after Hart's rambling on aliens.
Appearing about once a season is Steve Mahanahan, owner of Steve Mahanahan's Child Clown Outlet. Steve is hyperactive and wacky in his adverts, nothing particularly creepy. His child clowns—real children dressed as clowns—are extremely unnerving though. The worst moment was in season 3, where Mahanahan shows a VHS on child clown care, the clowns being treated like animals, forced to perform tricks, kept awake with bullhorns, and sprayed with poison (again, real children were used in this sketch). The VHS is of terrible, almost bootleg quality with grainy film and skipping music, giving it a horribly authentic feeling. If this doesn't convince that Mahanahan is a monster, the fact that he was molesting the clowns and he was implied to be abducting children to turn into his clowns will.
As if Steve Mahanahan wasn't bad enough, then there's his father Donald Mahanahan, who forced Steve and Mike into the child clown business. He owns "the original child clown outlet," and he openly admits all of the child clowns are his own children, "breeding them" with several women (with clown traits). Although he admonishes Mike for molesting the clowns, he also openly admits to luring the child clowns into touching him. And if that still wasn't bad enough, he openly beats up the (fake) child clowns for not behaving and tells us he's going to put them in cages they can't see through. He also has no regard for the lives of his children: when a (real) child clown starts crying, he says, "I think we'll have to bury this one in the back," and when he brings up what happened to Mike, he proudly proclaims he got shot in the face as if he deserved it.
The Lazy Horse Mattress advert. Starts out as one of the many tacky, low-budget fake adverts that fill Awesome Show, then abruptly turns into a blood-soaked nightmare scene.
"Ooh Mamma!" Tim and Eric, either playing children or manchildren, simply repeat "Ooh Mamma!" over and over as they play while their mother looks on, smiling. Tim and Eric become increasingly violent, smashing furniture up, and the already weird music turns into an Ominous Music Box Tune. The scene is then randomly intercut with Tim and Eric laughing normally while looking at an overhead projector, saying something about "Good tennis!", and shots of them playing again. Then Tim's head is replaced with his mother's head. Even by Awesome Show! standards it's bizarre, and the entire sketch has a lingering uneasy feeling about it.
It's Not Jackie Chan! One of the men playing this ridiculous game presses a buzzer when his friend messes up...and keeps on pressing it, the buzzer droning on and on, his friends clutching their heads in pain. The man grins into the camera, and his grin slowly fades into blank look, just staring at the viewer. Subtle compared to many other scenes, but very unnerving.
Tim:[now a disembodied head] ...well, I suppose I deserved it... [spits out blood]
[cut to credits]
"Crows" has Tim and Eric's eyes pecked out by crows. It's supposed to be a parody of Birdemic (in fact, Tim & Eric are largely responsible for finding Birdemic its audience), but the eyeless makeup is so grotesque it's horrifying. The gigging blind man with Black Eyes of Evil didn't help things at all (until he turns into toilet).
Patrick Duffy's "Man Nip", marketed as cat nip for men. However, when we see the world from the nip-takers perspective, Patrick Duffy turns into a demon who repeatedly says Duffy and his co-host tells him, "You're going to Hell!," in a deep voice. He screams, but when we cut back to outside, he looks like he's playfully rolling on his back life a cat, and Duffy and his co-host comment on how playful and peaceful he looks.
The Chrimbus Carol sketches. Carol gets angry at Mister Henderson for not being sadistic enough to her while his head is under a guillotine blade. Instead of taking his head off in a comical fashion, the blade cuts halfway through his neck and he lies there in agony, thrashing and coughing up blood. It's absolutely horrifying how realistic it is.
And once Mr. Henderson recovers, he's not happy with the fact that Gary (the brother of Larry, who committed suicide in a previous series), has been cheating with Carol. He comes back into the office with his voice unnervingly perishing, croaky and whispery, beats Gary to death in There Will Be Blood-like fashion, and then tells Carol how brutally and sadistically he's going to sexually use her for Chrimbus, all in the croaking voice, until he finally regains his voice and shouts "CAPICE?!" Thankfully, this is what Carol wanted all along...so hooray?
Pierre getting frostbite when he gets lost in the snowy woods. His fingers blacken, and he saws off his hand and leg, the blood now black sludge. Then his face ages and decays graphically, his nose rotting off by the end. They even put the final "Great job!" message over it so we can take a nice, long look at Pierre's ruined features.