Leroy Ye 7 months ago. Alan Jackson cheated. No word that it was Faith Hill they say it was pretty blond background singer. 0 Best Answer: I haven't heard about this one - why do you ask?? You've heard something???. I just heard about this recently too. Stacey Brooks, who works. It is believed all over Nashville that Alan Jackson did indeed have an affair with Faith Hill . That affair broke up his marriage but they later reconciled.