CMT Hot 20 Countdown is asking country stars some awkward questions this week.

Have you ever wondered what kind of underwear Jason Aldean prefers? Prepare to find out.

Meanwhile, Tim McGraw, Lady Antebellum and Kenny Chesney also get blindsided with unusual talking points.

"That's an odd question. Don't you think that's odd?" Chesney asks while host Katie Cook cracks up laughing.

Plus, Hot 20 goes behind the scenes and onstage at the Chicago stop of Kip Moore's CMT on Tour: Up in Smoke. Moore, Charlie Worsham and "Leave the Night On" star Sam Hunt show viewers what it's like to be on the road at the famous Joe's Bar location in the Windy City.

Catch it all and find out which music video tops this week's list on CMT Hot 20 Countdown on Saturday and Sunday (Oct. 18-19) at 11 a.m. ET/PT.