The Former Devil's Advocate

Despite the MANY implications my art may showcases, Nate and Leonard have only ever been co-workers (though Nate was hoping they could be more before he knew who Leonard truly was).

Leonard was the one who talked Nate into taking the job working for the Devil, having left out the finer details of what he’d be doing until Nate had officially signed an employee contract and was locked in to the job for a minimum of a year. Ashamed, panicked, and terrified of what he had agreed to do, Nate attempted to break his contract by sending out multiple contracts to their debtors, and Leonard, having been the one to bring Nate into the fold, was tasked with punishing Nate for the mistake.

After this moment, Leonard became emotionally and mentally abusive towards Nate, taking out his anger on Nate and emotionally beating him down so much that Nate was too afraid to quit when his year was up. Eventually, Leonard’s grudge became less about Nate’s mistake and more about the fact that Nate would just roll over and take any abuse that was thrown at him; Nate’s spinelessness disgusted him, and Nate was too afraid of Leonard to stand up for himself.

Mike Feedbach is a toon with a very, VERY strong sense of right and wrong. Having grown up an only child of a single mother (his father passed away when he was too young to remember him), he would often get picked on by bigger kids for being small and easily riled up. Eventually, he channeled that energy into practicing law, getting into a prestigious school on a sports scholarship. It was there he met his college sweetheart, Daisy Mae Petalton.

Mike eventually graduated college and earned his license, but shortly after doing so, Daisy Mae left him for a mutual friend that she felt had better prospects and understood her better; in the letter she left Mike, she explained that he was both too much and not enough for her. This loss sent Mike down a spiraling path of despair where he took actions that he is deeply ashamed of. By the time he pulled out of that downward spiral, he was broke, had lost his job, and had to move somewhere he could afford to live (in D&D it’s Inkblot City, in Cuphead it’s the Inkwell Isles).

It was during his move that he he heard about a devil making deals and stealing souls. Driven by an urge to redeem himself, and possibly prove Daisy Mae wrong, Mike focused all his energy on building a case to bring the devil to court and persecute him for illegally trading souls. This is also around the time where he met Nate and they start their rivalry which eventually becomes a friendship.

The lore sort of splits here and varies depending on the canon that he’s in, but in most lore, he manages to build his case and take the Devil to court, where he is then betrayed by Nate and ends their friendship. In the D&D lore, Mike is then killed and trapped in Hell, where he is later rescued by Nate and his friends. In Cuphead, it’s not nearly so dire.

Original, Ascended, Corrupted, Fallen

“What if I’m too far gone? What if I’m just no good? What if I’m a bad toon?”

“You’re my friend, and I don’t make friends with bad toons.”

Hindsight is 20/20