2005: Cheech debuted in CHIKARA in 2005 alongside his long-time tag team partner Cloudy, initially representing Special K and ROH before they left the company and became full-time members of the CHIKARA roster. As a rudo duo the two didn't advance much up the card, although they did engage in a wild feud with ROH students Matt Turner and Anthony Franco that saw Cheech execute a Shooting Star Press off a speaker.
2006: Continuing where they left off, Cheech and Cloudy failed to make much progress as a team, unsuccessfully challenging for the CZW Tag Team Titles and falling out of Tag World Grand Prix in round 2. However, change came in mid-2006 when, following a loss to the North Star Express, the two shook the hands of Corbin and Cruz and embraced the tecnico side. Cheech also had a remarkable run in that year's Young Lions Cup, making it all the way to the final before losing to Arik Cannon following a Burning Hammer. The tournament saw Cheech debut a new finisher, the Deluxe (later Go 2 Cheech), a move which he would use multiple times over the course of the weekend. At the year's conclusion both Cheech and Cloudy donned outfits and became Incoherencito, with Cloudy playing Hallowickedcito and Cheech playing Deliriouscito
2007: King of Trios weekend saw Cheech and Cloudy gain the three points required to challenge for Los Campeonatos, but they fell in an epic match to F.I.S.T. in April. A few months later they reprised their masked roles by allegedly portraying two other members of the Delirious family in a match against the Colony. The year ended with yet another championship failure, falling to of all the teams Incoherence in a great match.
2008: Cheech and Cloudy would make very few appearances in the first half of 2008, finally reappearing on CHIKARA's return to the New England area. Soon after the two began to portray “surfer” personas, adopting slightly modified names, wearing shorts and unbuttoned shirts to the ring, and using such moves as the surfboard to much success.
- Finishing and signature moves
- Go 2 Cheech
- Busaiku Knee Strike
- Stalling Slingshot Somersault Senton
- Fosberry Flop
- "The New Wave"
- Tag teams and stables
- Cheech & Cloudy with Cloudy
- Up in Smoke with Cloudy
- Lacey's Angels with Cloudy, Deranged, Izzy, Lacey
- Miracle Ultraviolence Connection with Cloudy, Brodie Lee
- Special K with Abyss, Angel Dust, Becky Bayless, Brian XL, Cloudy, Dana Dameson, Deranged, Dixie, Hijinx, Hydro, Izzy, Jody Fleisch, Joey Matthews, Krazy K, Lacey, Lit, Mellow, Mikey Whipwreck, Slim J, Slugger, Yeyo