Adam recalled a funny story about an incident that happened when he and Jimmey were just starting out in radio. Adam explained they were sharing a room in some crappy hotel and the shower drain didn't work very well, causing the tub to fill as the shower ran. Since Jimmy took the first shower, Adam was forced to shower in six inches of his waste water, and add insult to injury, halfway through his shower, Jimmy knocked on the door to inform Adam that he might have jacked off in the shower.
That, however, was nothing compared to the Natalie Maines prank Jimmy pulled on him. Years ago, Natalie Maines asked Adam to escort her to the Grammy Awards and Adam agreed, despite having a serious girlfriend at the time. The next day Adam received a bouquet of roses from Natalie, thanking him for going with her, and a few days later he got a giant chocolate chip cookie from her. Finally, he got a box from her containing an "obviously worn" pair of panties along with a note saying, "We need to F'. NOW!"
Adam said he turned to Jimmy for advice and Jimmy told him he needed to contact her immediately and tell her to stop. From his cubicle office, Adam called Natalie, who angrily insisted that she had nothing to do with any of the gifts he had received...that's when Adam looked up to see a smiling Kimmel videotaping the whole conversation.