- May 11 Sabrina Carpenter, American actress (Girl Meets World) and singer, born in Lehigh Valley, Pennsylvania
- May 23 James Charles [Dickinson], American internet personality and model (Cover Girl), born in Bethlehem, New York
- May 25 Brec Bassinger, American actress (Stargirl), born in Saginaw, Texas
- May 27 Lily-Rose Depp, French-American singer and actress (The Dancer), born in Neuilly-sur-Seine, France
- May 28 Cameron Boyce, American actor (Mirrors, Jessie), born in North Hollywood, California (d. 2019)
- May 30 Guanyu Zhou, Chinese racing driver (first Chinese F1 driver), born in Shanghai, China
- May 30 Sean Giambrone, American actor (The Goldbergs - "Adam"), born in St. Joseph, Michigan
About May 1999
How Old? 23 years old
Generation: Generation Z
Leap Year: No