1998
2000 
Production and Director
The Best Production award for 1999 goes to Apple Tree Theatre's Shakespeare's R&J, a stirringly original vision of Romeo and Juliet written by Joe Calarco. Four anonymous 1950s public-school boys enact Shakespeare's tragedy as a rebellious late-night adventure but find their performance becoming a deeper expression of defiance as well as an assertion of individuality.
The Best Director award for 1999 goes to Joe Calarco for Shakespeare's R&J at Apple Tree Theatre, in a close race with a pair of Illinois Shakespeare Festival directors, Karen Sheridan for The Merry Wives of Windsor and Patrick O'Gara for Richard III. Calarco's direction of his own 1997 original play - and his handling of a young ensemble of four performers - is spare, clean, and insightful, resulting in a fresh and profoundly moving production.
Performance
The Best Actress award for 1999 goes to Lisa Dodson as the aging temptress Cleopatra in Chicago Shakespeare Theater's inaugural Antony and Cleopatra. Dodson's petulant prima donna behaves in fear of advancing age and fading charms, clinging to Antony's devotion as evidence of her own vibrancy.
The Best Actor award for 1999 goes to Jay Whittaker for his title role in Richard III at the Illinois Shakespeare Festival. Whitaker's ghoulish Duke of Gloucester - ghastly pale in white-face, with darkened eyes and a red mouth like a slash across his face - is clad entirely in black, sporting the typical crook back, curved foot, and withered arm, and resembles the super-villain Joker from Batman.
The Best Supporting Actor award for 1999 goes to Frank Nall for his blustering vein-in-the-forehead Ford in the Illinois Shakespeare Festival's The Merry Wives of Windsor. Nall's insanely jealous husband seethes and sputters, and pants and puffs, in an energetic comic turn.
The Best Supporting Actress award for 1999 goes to Michelle Giroux for her fiery, almost Irish Helena in A Midsummer Night's Dream at the Stratford Festival of Canada. Not the typical bookworm Helena, Giroux's auburn-haired firebrand evidences physical as well as inner beauty.
Technicals
The Best Scenic Design award for 1999 goes to Ruari Murchison for the narrow but deep staging for West Side Story at the Stratford Festival of Canada, using scrims and walls to frame illustrative stage portraits. A pair of eight-foot chain-link mesh cages ingeniously adjust to become fences, walking paths, the door to Doc's Drugstore, even basketball backboards.
The Best Costume Design award for 1999 goes to Jordan Ross for a colorful A Midsummer Night's Dream at Court Theatre. Puck is a leather-clad punk rocker, attired in a sleeveless black vest, red velvet pants and cap with knee-high boots, and the female fairies resemble the Spice Girls - spiked hair of various florescent colors and patched and tattered bell-bottoms - and the dweebish Lysander wears lavender, while a pony-tailed Demetrius is attired in blue with a collegiate scarf
The Best Lighting Design award for 1999 goes to Christopher Akerlind for Richard III at the Illinois Shakespeare Festival, lighting the sickly King in shades of yellow and evoking a surreal battle at Bosworth with swirls of spotlights, red light, and stage fog.
The Best Sound and Music Design award for 1999 goes to Keith Handegord and Don Horsburgh for the Stratford Festival of Canada's kind-hearted A Midsummer Night's Dream, with an array of effects and a genial original score that concludes with the woodland fairies gathered to sing "Break of Day" in a benediction of the three newly wedded couples.