The Artist Pursuit of Being Yourself 2008 was a wrestling event produced by CHIKARA (CHIKARA). It took place on September 20, 2008 from the Streamwood Park District Community Center in Streamwood, Illinois. The event was CHIKARA's first event ever in Illinois.
Numbers in parentheses indicate the length of the match.
- Dark NWA Midwest Heavyweight Title Match: Silas Young defeated Egotistico Fantastico to retain the NWA Midwest Championship
- Silas Young retains the NWA Midwest Heavyweight title after landing the Zero Gravity.
- Tag Team Match: Lince Dorado & Helios defeated The Thomasellis (Brandon Thomaselli & Vito Thomaselli (9:34)
- Lince and Helios win in 9:34 with stereo Shooting Star Presses.
- Buck gets the win with a cradle, pulling the tights to get the cheap win.
- Eight Man Tag Team Match Match: Da Soul Touchaz (Acid Jazz, Marshe Rockett & Willie Richardson) & Trauma defeated Crossbones, Sami Callihan, Trik Davis & UltraMantis Black
- Marshe was trapped throughout the match by the rudos, but Willie drops the Bomb with the legdrop for the win.
- Colin defeated Jimmy via the F-U after Vin distracts Jimmy by throwing an Equinox mask at him.
- Incognito catches Aguila de Oro with a modified reinera.
- STIGMA defeated Drake with a tombstone piledriver after Drake was shoved into Vin Gerard.
- Vin locks in the STF to get the win.
- Ten Man Tag Team Match: Amasis, Gran Akuma, Mike Quackenbush, Player Dos & Soldier Ant defeated Hallowicked, Icarus, Ophidian, Player Uno & Worker Ant (31:10)
- Player Dos pins Hallowicked for the fall and win.