1997
1999 
Production and Director
The Best Production award for 1998 goes to Play On! at the Goodman Theatre, an inventive remounting of the Broadway musical version of Twelfth Night featuring two dozen newly arranged songs by Duke Ellington and reset in swing-era New York City. Shakespeare's play is stripped down but literally jazzed up, an enormous entertainment set within Lady Liv's notorious Cotton Club.
The Best Director award for 1998 goes to Sheldon Epps for the Goodman's Play On!, a masterful mélange of swing-era music played live onstage, new choreography by Duke Ellington's granddaughter, and an array of colorful characters within the familiar Twelfth Night romantic entanglements, all staged upon a towering set of reflective beveled mirrors.
Performance
The Best Actress award for 1998 goes to Tandy Cronyn for her central Margaret in Jeffrey Sweet's ambitious new adaption of the Henry VI trilogy, The Falcon's Pitch, at the Illinois Shakespeare Festival. From the youthful defiance and raven-haired beauty of the first act, through political romance and ruthless power-mongering, Cronyn's fiery heroine transforms through tragedy into a wild-eyed curser of the York family.
The Best Actor award for 1998 goes to Brian Bedford in his role as Benedick in the Stratford Festival of Canada's stately Much Ado About Nothing. Bedford's long-haired and bearded bachelor becomes the suave and clean-cut leading man in a refreshingly comedic seizing of the opportunity of renewal through love.
The Best Supporting Actor award for 1998 goes to Paul Oakley Stovall as the Malvolio-like reverend Rev in Play On! at the Goodman Theatre. Stovall's yellow-shirted and suspendered villain Rev stops the show with a wrenchingly poignant singing of "Don't You Know I Care" and wins the heart of Lady Liv despite his comical chicken walk.
The Best Supporting Actress award for 1998 goes to Tonya Pinkins as the Olivia-styled Lady Liv in the Goodman's spectacular Play On! Pinkins' memorably melancholy performance features serious acting chops as well as brilliant jazz singing, from "Mood Indigo" to "Don't Get Around Much Anymore" and "Black Butterfly" as well as the show-defining, "I Ain't Got Nothin' But the Blues."
Technicals
The Best Scenic Design award for 1998 goes to Dex Edwards for the spacious Mediterranean courtyard in Shakespeare Repertory's The Comedy of Errors. Edwards stages the comedy with upstage marble arches, climbing vines, and white-wire deck chairs to present an authentic Italianate backdrop for the frantic farce.
The Best Costume Design award for 1998 goes to Marianna Elliott for the swing-era New York fashions of Play On! at the Goodman Theatre. From Vy-Man's striped dress and striped three-piece suit to the eight purple-and-black clad tap-dancers accompanying Lady Liv in her indigo gown, the costumes are jaw-droppingly colorful and authentic.
The Best Lighting Design award for 1998 goes to Charles Jolls for the gloomy and sepulchral mood in the Next Theatre Company's Cardenio. Jolls' effects enhance the texture of the quasi-Shakespearean production with a courtyard lit in tones of burnt orange and muted yellow, a flickering torches and shadows-heavy church sanctuary, and the stark white creepiness of an underground crypt.
The Best Sound and Music Design award for 1998 goes to Robert Neuhaus and Henry Marsh for the sound effects and original songs and music in Shakespeare Repertory's post-Revolutionary War version of Much Ado About Nothing. The songs further enliven an already light-hearted production, especially the drums and reeds accompaniment to the returning soldiers' "Lift A Glass to Those We Left Behind."