The Donald elicits a strange set of mixed emotions within Stewart. On one hand, the loudmouthed egomaniac is such a cartoonish figure that it's very easy for The Daily Show just to treat him like the joke he is. (And in the past, Stewart and Trump had a congenial rapport on the show, with the billionaire proving to be a lively guest.) But as Stewart prepares to head off into the sunset, he's been both wistful and appalled by Trump's brash climb to the top of the GOP presidential polls. (Ridiculing Trump's bizarre escalator ride down to his press conference where he'd announce his candidacy, Stewart opined, "I haven't seen an entrance that majestic since my friend met me at the Gap after grabbing an Orange Julius.") In recent months, Stewart has looked quite happy to leave the anchor chair behind. But as Trump gave him day after day of risible, ridiculous material, the long-running host almost seemed sad to be hanging it up. Almost.