- May 1 "On the Waterfront" opens at Atkinson Theater NYC for 8 performances
- May 1 "Sold (The Grundy County Auction Incident)" single released by John Michael Montgomery (Billboard Song of the Year 1995)
- May 2 "Hamlet" opens at Belasco Theater NYC for 121 performances
- May 3 "My Thing of Love" opens at Beck Theater NYC for 16 performances
Academy of Country Music Awards
May 10 30th Academy of Country Music Awards: Alan Jackson and Reba McEntire win