Kenny Chesney stopped in to hang out and co-host the Country Countdown USA radio show with Lon Helton over the weekend. Knowing Chesney and Taylor Swift are good friends, Helton played something she said a few weeks ago about Chesney: "He is one of the coolest, most affectionate, gracious people that I’ve met in the music industry, and he’s always reaching out to me to say 'hey' and check up on me and see how I’m doing. It seems like he has this weird intuition to know when I need someone to stop in and say, 'How are you.'"

The two country superstars are e-mail buddies, and Chesney will randomly send her a note to check in. Swift says that they always seems to come at the right time when she’s having a rough day.

When Helton aired these words from Swift, Chesney responded, "Taylor and I are very good friends and I've known her for a while, and I know the ups and downs that an artist goes through." He went on to say that the year before she first won Entertainer of the Year, she was slated to open for him on tour -- but there was a problem.

That was the first year his tour would be sponsored by Corona, and according to the ‘Somewhere With You’ country star "there was some sort of legal, contractual thing where people weren’t comfortable with having an alcohol sponsored show and having a 17 or 18-year-old on the show. So, I had to call Taylor and tell her that she couldn’t do that tour. And I gave her, as a ‘I’m sorry’ present, I gave her a lot of money."

The next year, she got nominated for Entertainer of the Year the same year as Chesney, and she won. Laughing, he told Helton, "So, I’m backstage and I come up behind her and gave her a hug and said, 'I want my money back' ... I haven’t gotten it back yet, but maybe I will one day, who knows."

As previously reported, Chesney’s Goin’ Coastal Tour kicks off on March 17 in West Palm Beach, Fla. with Uncle Kracker, Billy Currington and Zac Brown Band. He also just had his 21st No. 1 song with 'Somewhere With You.'