Joining a very exclusive list of comedians, Dane Cook sold-out Madison Square Garden in 2006 and was only the second comedian ever to reach the Top 5 on the Billboard Hot 100 chart. However, by the end of the decade he was overhyped, overexposed, and liking him became as uncool as liking Nickleback.

From maligned films such as "Simon Sez" and "Good Luck Chuck," to the unaired sitcom "Next Caller,” Cook failed to make it as a leading man in film and television. Not everyone can be Jim Carrey, but Cook’s stage charisma did not translate to film, and once on camera, he was just another schlub.

His half-brother and former business manager, Darryl McCauley, and his wife Erika confessed to embezzling twelve million dollars from Cook. McCauley was sentenced to six years in prison, his wife was sentenced to three, and both received lengthy durations of probation.

Louis C.K., who has also been persona non grata as of late, accused Cook of plagiarism many times, even working it into a Season 2 episode of FX's "Louis." Cook denies the allegations and despite C.K.'s tarnished image, many people still associate Cook with joke thievery.

Cook hasn’t completely disappeared, in 2019 he embarked on a national tour, and in May 2021, he performed at the Laugh Factory's post-pandemic reopening night. While he may never reach his former glory, Cook has amassed enough fans to support a touring career for the rest of his life.