Enamored by the super model, O'Brien begins the long-running Conan segment by sitting down with Upton for a nice champagne-filled dinner.
As the pair pick up their controllers and experience the co-op game, O'Brien suggests that they share a controller in an attempt to get closer to Upton and to better take on the title's challenging boss battles.
After completing the level together, O'Brien said it felt like they had become one person.
"I was able to help you experience winning," Upton joked.
Cuphead, developed by Studio MDHR, features a unique look inspired by cartoons of the 1930s as players work together to shoot down enemies as either Cuphead or his partner Mugman. The title is set for release on the Xbox One and PC on Sept. 29.