Headly is often cast as devoted mothers, wives and friends in upper middle-brow dramatic fare, thoughtful comedies, and the occasional odd film. Headly was the concerned mother of a lonely dreamy girl in the outstanding fantasy "Paperhouse", worthy foil to conmen Michael Caine and Steve Martin in "Dirty Rotten Scoundrels" (both 1988), Tess Trueheart in "Dick Tracy" (1990), and the feisty wife of Bruce Willis in "Mortal Thoughts" (1991). On TV, Headly appeared with Robin Williams in an acclaimed "Great Performances" presentation of Saul Bellow's "Seize the Day" (PBS, 1987) and earned an Emmy nod for her work in the Western epic "Lonesome Dove" (CBS, 1989). Subsequent credits include the direct-to-video children's drama "Ordinary Magic" and, back on the big screen, "Getting Even With Dad" (both 1994), with Macaulay Culkin and Ted Danson and Stephen Herek's "Mr. Holland's Opus" (1995), as Richard Dreyfuss' wife. Headly had a banner year in 1996 with roles in the ensemble Tarantino-noir style "2 Days in the Valley;" the Anjelica Huston-directed Southern drama "Bastard Out of Carolina;" and as Steve Martin's love interest in the misguided film remake of the TV classic "Sgt. Bilko."

The actress then spent the 1996-1997 season playing Dr. Abby Keaton on NBC's hit medical drama "ER" before being cast on Nathan Lane's ill-fated sitcom "Encore! Encore!" (NBC, 1998) playing the sister of Lane's opera tenor (her subsequent TV highlights included a turn opposite Stanley Tucci's Walter Winchell in the above-average 1998 HBO biopic "Winchell;" the 2001 miniseries "A Girl Thing;" and the Jane Fonda role in a 2001 TV remake of "On Golden Pond" directed by the original screenwriter Ernest Thompson).

Back on the big screen, Headly appeared in such varied fare as Mike Figgis' experimental, multi-screen drama "Timecode" (2000),