Jon Stewart examines Donald Trump's deadline to come up with the $454 million bond in his civil fraud case, and deconstructs investment talking heads like Kevin O'Leary calling Trump's actions a "victimless crime." Plus, Gary Clark Jr. sits down with Jon to discuss his new album “JPEG RAW." He opens up about his candid new song “Habits,” collaborating with Stevie Wonder and George Clinton, and how time spent alone gave him the freedom to branch out musically.