Imagine if your half-brother swindled millions of dollars from you. Then imagine if Jeopardy used that incident as fodder for a question.

That’s exactly what happened to comedian Dane Cook recently, when his half-brother Darryl McCauley, who went to jail for embezzling funds while serving as Cook’s business manager, was the subject of a question (or rather, an answer) on the long-running game show.

Cook tweeted a video featuring his response to the moment Sunday, with the caption “#mylife.”

The video begins with Cook joking, “I love Jeopardy, I can just watch it and get away from it all,” before cutting to the awkward moment when Alex Trebek says, “Dane Cook’s half-brother and business manager stole millions from the comic, this crime of misappropriating bank funds.”

When the contestant correctly answers, “What is embezzlement?” a deadpan Cook turns the camera back on himself and sighs in disappointment.

McCauley, who served as Cook’s manager from the early 1990s through December 2008, was convicted in 2010 of stealing millions from the comic and sentenced to five to six years in prison, the Boston Globe reported at the time. According to the paper, McCauley pleaded guilty to 27 counts of larceny over $250, three counts of forgery, embezzlement, and other charges. He was also ordered to make restitution to Cook.

Watch Cook’s video above.


America's favorite answer-and-question game.

  • TV Show