Those who find Chesney funny may appreciate his self-deprecating sense of humor and his ability to poke fun at himself and others. They may also enjoy his energetic and outgoing personality, which often comes across in his live performances and interviews.
On the other hand, those who find Chesney annoying may find his humor to be too over-the-top or silly. They may also be put off by his sometimes loud and boisterous personality.
Ultimately, whether or not you find Kenny Chesney funny or annoying is a matter of personal opinion and there is no right or wrong answer.