The Last Five Years was first presented by Northlight Theatre (B.J. Jones, artistic director, Richard Friedman, executive director) at the North Shore Center for the Performing Arts, Skokie, Illinois, on May 23, 2001. The final performance was July 1, 2001. Set and costumes by Beowulf Boritt, lighting by Christine Binder, sound by Rob Milburn and Ray Nardelli, casting by Mark Simon, musical direction by Thomas Murray and direction by Daisy Prince. The role of JAMIE WELLERSTEIN was played by Norbert Leo Butz and CATHERINE HIATT was played by Lauren Kennedy. The stage manager was Patty Lyons.
The first New York production was presented by Marty Bell and Arielle Tepper, in association with Libby Adler Mages/Mari Glick and Rose/Land Productions, at the Minetta Lane Theater on February 11, 2002. Press opening was March 3, 2002, and the final performance was May 5. The designers were the same as the Chicago production, except the sound designer, Duncan Edwards. The role of CATHERINE was played by Sherie Rene Scott.