|Portrayed by Mae Laborde|
"The Nightman Cometh"
"The D.E.N.N.I.S. System"
Gladys is an old woman that the Gang uses in their various schemes.
Gladys is often confused and prone to making non-sequitur comments. Just before accompanying Charlie's musical on the piano, she mentions that she once knew Calvin Coolidge. ("The Nightman Cometh") When Dennis takes her to the fair to act as his grandmother she repeatedly mentions how her grandmother was a lesbian who had an affair with Susan B. Anthony. ("The D.E.N.N.I.S. System")
- In the live performances of The Nightman Cometh, the role of Gladys was played by Rhea Perlman,
the real-life wife of Danny DeVito.