Like Judd, both singers are huge Kentucky sports fans. Montgomery, who lives in Boyle County, made sure Wednesday's UK-Austin Peay game was put on the video screens inside Rupp Arena before he would leave his TV set for final rehearsal before the concert.
"The game had already got way too close and no way was I going to miss out on the final minutes," Montgomery said before his concert. "These people have to learn not to bother me when UK is playing. That's my team."
A loss to Louisville or Wednesday's lackadaisical 61-53 win over Austin Peay won't change the way Montgomery or Gentry feel about their Wildcats. They made numerous references to UK during their concert, had former UK quarterback Tim Couch on stage to sing with them, and still plan to record a song about their favorite college team.
Don't worry about the UK students in the E-Rupp-tion zone relating to Montgomery Gentry, either. The concert crowd covered all age ranges, but clearly they are a favorite with college-age fans.
Montgomery and Gentry could perhaps tell the players about not taking their success for granted, because they haven't.
Montgomery seemed to have had half of Boyle County as his guests at the concert and he proudly wore his Boyle County hat around Rupp Arena while pre-concert arrangements were made.
It was shocking to hear UK's Chuck Hayes explain what happened to the Cats Wednesday when they gave up 41 points the second half after yielding just 12 in the first half and let Austin Peay cut a 17-point lead to three with almost three minutes to play.
"At halftime everybody was praising each other, our deflections were up and we were playing great defense," Hayes said. "Then I guess we just relaxed. We thought they would lay down and take the loss. They surprised us."
Surprised us? How could a Kentucky basketball team think any team was going to "lay down" just because it was playing the Wildcats?
There was no relaxing during the Montgomery Gentry performance. It was all fast-paced, the same kind of style that Tubby Smith's team wants to play but has had trouble doing the last few games.
The Montgomery Gentry concert was also in perfect sync, something that cannot be said about the offense UK has displayed during the second half of a loss to Louisville last Saturday or second half of Wednesday's win over Austin Peay.
The Cats have players unsure when to shoot (Antwain Barbour, Kelenna Azubuike), some that are taking poor shots (Gerald Fitch, Cliff Hawkins) and some having trouble getting their best shots (Erik Daniels, Chuck Hayes).
Lack of depth? It was no problem for Montgomery Gentry. They went out and recruited Charlie Daniels, Phil Vasser and Dierks Bentley to be part of their show and Montgomery even brought in his brother, John Michael Montgomery. That's quality depth, something UK doesn't have and something that is starting to be a serious problem.
Montgomery and Gentry also had fun starting with Montgomery's leap on to the stage and continuing with an extra long performance.
"They think we are stopping at midnight, but we're not. We're going on," Montgomery said before the music continued.
Kentucky's players just seem to have lost some of their spark. Maybe it was too many marquee games in a row. Maybe it was the team's lack of depth. Maybe it was just losing to Louisville.
Whatever the reason, Kentucky better get the same pizzazz that Montgomery Gentry had Wednesday or there's no way Rupp Arena is going to be nearly as much fun for fans Saturday when the Cats play North Carolina as it was for fans at the New Year's Eve concert.