CKY2K, the second film in the CKY series, was released on May 22, 2000. The video features a trip to Iceland, the rental car, a baseball game, "Bran's Freestyle", and other random items. The music features early versions of Flesh into Gear and Sporadic Movement by CKY; as well as many other artists, including an opening scene with Rammstein, Iceland scenes with Björk and Orbital, and a skateboarding scene with Aphex Twin. Near the end of the video, there is a scene in which a minor exposes his genitalia in front of a public restaurant. The video explained that "this is what happens when you tell Bam you'll do anything to be in CKY." In 2003, the parents of the minor sued. During the hearing, a County Court Judge ruled that images of the plaintiff "must be deleted from future versions" of the video. Subsequently, CKY2K was discontinued due (in part) to copyright issues. The first major issue was from Björk. Iceland The video was notable for the documentary of their trip to Iceland. The music features "Hyper-Ballad" by Björk where Bam and the crew hang out on the top of a mountain with gorgeous views from the top. As they stayed in a hotel somewhere in Iceland (the hotel at the airport), Brandon Dicamillo smeared feces on Ryan Dunn while he was sleeping on the bed. Smeared with feces, Ryan fought back by urinating on Brandon sleeping on the floor. Later, they argued in the car about the incident. The crew does a variety of stunts, including guys riding on furniture on the road as a sled, featuring music by Orbital playing "Halcyon + On + On". Later, Bam was outside Björk's house calling her. The rental car Bam drives a Chevrolet Cavalier after paying $9 for extra insurance. With the car, Bam attempts crazy reckless driving maneuvers, knocking over orange cones and skidding turns. The next day, Rake Yohn finished off the already damaged car by setting fire to the radio, which completely burned the entire car. The music features an early version of Sporadic movement by CKY

CKY 3, the third film in the CKY series, was released in 2001. Soon after its release Margera and DiCamillo were sued over the fight scene involving Mike Vallely. The issue was settled out of court in 2006. It was also the first of the videos to be taken off the market due to copyright restrictions. Some of the musicians (or their legal representation) were unhappy with Margera using their music without their permission. This would later happen with CKY2K and the box set including all three videos and the documentary.

CKY4: The Latest & Greatest CKY 4, the fourth film in the series, was released on November 10, 2002. It has a marked improvement in editing techniques compared to the other films, mostly due to Bam Margera's newly-acquired wealth and ability to purchase motion picture film cameras and utilize advanced post-production facilities. However, it also features a lot of older video material, some unseen, some extended and some off-cuts from previous CKY films. Scenes include Don Vito's 50 Shots of Peach Schnapps (Bonus Feature) and Ryan Dunn rolling off a roof in a barrel. CKY4 is the only CKY video to be censored, and one of the few DVDs to have been censored three times. ▪ A DVD Easter Egg showed Bam and his then-girlfriend mid-coitus with altered color mixes to avoid nudity. This wasn't the first time CKY videos have attracted trouble of this sort, but none of the previous videos cut legal sexually themed scenes until this one in mid-2003. ▪ In 2002, Brandon DiCamillo and CKY drummer Jess Margera wrote a rap about Masters Of The Universe characters Skeletor and Beast Man engaging in extreme homosexual behavior, called Skeletor vs Beastman. Mattel, owners of the Masters Of The Universe franchise, heard about the rap, and were displeased. Margera was sent a cease-and-desist order, and subsequent editions of the DVD have replaced this video with skateboarding footage. ▪ CKY guitarist Chad Ginsburg, a large fan of punk rocker G.G. Allin, visited his grave one day and after consuming an entire bottle of Jim Beam bourbon (Allin's favorite beverage), he proceeded to urinate on the grave, and left an autographed copy of Infiltrate.Destroy.Rebuild. which was later stolen. Mixed in between the grave footage is CKY performing Allin's song "Bite It, You Scum". ▪ At the end of the "lil key key" skit performed by Chris Raab, there was a "Secret Easter Egg" also got cut in 2003 for unknown reasons.