Tattoo was a prisoner and boss in Dead to Rights.
While awaiting his execution in the Iron Point Penitentiary, Jack Slate is informed by Preacherman Jones that Tattoo has an escape map and is planning to make a prison break during Jack's execution. After getting the battery acid from Wireboy, Jack goes after Tattoo in the showers where he is discussing how he has gotten Gofer to drive getaway for him. Jack demands to see Tattoo's map, but Tattoo refuses. Tattoo, his two goons and Jack fight and Jack ultimately beats Tattoo, stealing his escape map. Guards arrive moments later looking for Jack on Sickle's behalf, but the annoyed Tattoo lies to them about seeing Jack. Later, as Jack reaches the end of the tunnels, he's surprised to find that Tattoo made it even without his escape map. Tattoo is recaptured and beaten by the guards before he can escape, creating a distraction that allows Jack to get out where he's nearly run over by Tattoo's getaway driver Marvin Silt. Jack is pleased by Tattoo's recapture as he feels Tattoo should not be loose on the streets.
Later, at the gold mining factory, Tattoo reappears armed with an M60 machine gun and backed up by a few armed prisoners. Jack kills Tattoo's men and engages Tattoo in a gunfight. Finally, Jack guns down Tattoo who tells Jack he'll see him in Hell as he dies. Jack then steals Tattoo's M60 and flees through the mining tunnels.
- Tattoo was the only game boss who had to be fought twice. He also had the distinction that the first time was hand-to-hand and the second time was with guns.
- Tattoo ultimately played a big role in Jack's prison break: Jack used Tattoo's escape map to find his way out, Tattoo's recapture distracted the guards long enough for Jack to get out of the tunnels and Jack used the car of Tattoo's getaway driver to escape the area.
- Tattoo doesn't appear to be particularly bright with at least Wireboy and Preacherman Jones being aware of his escape plan. Jack comments to Wireboy that "the man don't know how to keep his trap shut" and Wireboy responds that Tattoo isn't "the brightest star in the planetarium." Tattoo also openly discusses his plan in the showers, something Jack mocks him for. Jack is also surprised that Tattoo managed to make it all the way to the end of the tunnels "without his picture book to follow" after Jack stole Tattoo's escape map.