Nick's Best Worst Interviews Of 2016 [WATCH]

Toby Keith. The Band Perry. Kip Moore. They are just a few of Nick Kessler's victims from the past year in his video series on WGNA, "Worst Interview Ever." Check out his top-5 worst interviews!

I have never seen someone become so much worse at something after getting so much practice. But that is exactly what our Sunday afternoon host Nick Kessler achieved this year as we let him interview some of country's biggest stars. So here are the best of the Worst Interviews of 2016. Enjoy the awkwardness!

5. Kip Moore

Nick really built some negative momentum as he interviewed Kip backstage at SPAC in June. Kip confirms this by telling Nick it was the Worst Interview he ever had. With questions like "Would you duet with Celine Dion?" you can see this one spiraling to an uncomfortable place!

4. Cole Swindell

I think one moment pretty much sums this one up: Nick taking a phone call from his mom during the interview. Cole even ends up speaking with her. Enjoy!

3. The Cadillac Three

The guy's reaction in this one is priceless. They know something is definitely off at the get go, as Nick squeezes onto a sofa with all three guys. With questions and statements like "Why Cadillac? Why not Lexus Three?" and "You guys must use conditioner like crazy," this is one Nick's less stellar moments.

2. The Band Perry

Note to all country artists: If you are getting on an elevator and you see Nick following you, make sure the door closes before he gets on—or run. The Band Perry were in town for our Secret Star show in November and got cornered by Nick. As you know, they are brothers and sisters, and Nick gets this one going with the gem "How hard was it to start a band with all people having the same name Perry?" Do your homework, Nick.

And Nick's Best Worst Interview of 2016 is...

1. Toby Keith

This stellar moment in Nick's interviewing career took place on Toby's bus at SPAC in August. From mixing up Toby Keith's Bar and Grill with Jimmy Buffet's Margaritaville to Nick asking Toby "Why the make Red Solo cups?" and if he would sign his 'teddy,' this one takes the cake. Toby gives Nick some spelling and math lessons, and this is pure Worst Interview gold!

There you have it - Nick's 5 Best Worst Interviews of 2016. Here's to Nick continuing his downard spiral so we get more interviews like this in the new year.

To see all of Nick's Worst Interviews, click here.