In Sly Cooper: Thieves in Time, the Cooper Gang travel to the Wild West to encounter Sly's ancestor from the 19th century, Tennessee Kid Cooper. In Sly Cooper and the Thievius Raccoonus, members of the Fiendish Five steal and split up sections of the Thievius Raccoonus. Tennessee Kid Cooper's section was stolen by Muggshot, only to look at the pictures, and not even put the skills listed to use. After Sly defeated Muggshot and retrieved Tennessee's section of the Thievius Raccoonus, Sly read and learned about how Tennessee was an outlaw, stealing from rich landowners by carrying out old-style train robberies, as well as his skills of walking, running and sliding down the rails of railroad tracks to escape being caught. These skills are also used multiple times throughout the Sly Cooper series.
During Sly 4, Sly purposefully gets himself thrown in jail in order to meet Tennessee. When Sly informs him of who he is, Tennessee does not believe Sly at first. Sly later proves and convinces Tennessee of who he is by breaking out of the prison (with the help of Bentley). The Cooper Gang then helped Tennessee retrieve his gun from one of the mines, and then set out to take down the notorious Toothpick.