Trump says a peace deal with Iran is imminent, but he’s been making that claim for months. Jon Stewart examines Trump’s shaky record as a negotiator, despite his self-proclaimed status as the best in the world and argues that his "Art of the Deal" is really just the art of trolling. Plus, the Freedom 250 concert continues to unravel as more headliners drop out, and former TDS News Team correspondent Olivia Munn stops by with a heartfelt tribute that was definitely not intended for Stephen Colbert. Jason Bateman also joins Jon to talk about his new projects, Netflix’s Black Rabbit and HBO’s DTF St. Louis, sharing how the latter found its unique voice and reflecting with Jon on aging, fatherhood, and the loneliness of kids leaving for college.