Laying in the Gutter, Looking at the Stars 2008 was a wrestling event produced by CHIKARA (CHIKARA). It took place on September 21, 2008 from the West Park Party Center in Cleveland, Ohio. The event was CHIKARA's first event ever in Ohio.
- Numbers in parentheses indicate the length of the match.
- Hawke used a metal blade wrapped around his wrist to knockout Richardson and get the win.
- Icarus gets the pinfall via small package on Incognito.
- Jimmy Olsen gets the win with a piledriver.
- Tag Team Match Match: The Osirian Portal (Amasis & Ophidian) defeated Da Soul Touchaz (Acid Jaz & Marshe Rockett) (8:19)
- Acid Jaz was tranced when attempting the Swiss Mist, allowing the Portal to put Marshe in the way to let Jaz accidentally hit the Mist on Marshe.
- The confusion allowed the Portal to set up for the Osirian Sacrament for the Osirian Portal to get the win.
- Lince gets the win via shooting star press.
- Ten Man Tag Team Match: Mike Quackenbush, The Colony (Fire Ant, Soldier Ant & Worker Ant) & Tim Donst defeated The Unstable (Colin Delaney, STIGMA & Vin Gerard) & The Order Of The Neo Solar Temple (Crossbones & UltraMantis Black) (16:12)
- Fire Ant pins Vin Gerard for the victory following the Ant Hill.
- Claudio wins via Ricola Bomb.
- CHIKARA Campeones De Parejas Title Best Two out of Three Falls Match: The Super Smash Bros (Player Uno & Player Dos) defeated Incoherence (Delirious & Hallowicked) to become Campeones de Parejas (21:09)
- Delirious pinned Player Uno (2:45)
- Player Dos pinned Delirious (6:24)
- The Super Smash Brothers pinned Delirious (12:00)