Forming his own production company, Kelley created the critically-acclaimed, Emmy-winning "Picket Fences" (CBS, 1992-96), set in the fictional town of Rome, Wisconsin. He peopled Rome with a collection of mildly eccentric characters and mixed serious topics with extraneous, often silly subplots, the resolutions of the serious issues often ending up in the courtroom. Despite lasting much longer than the far quirkier "Twin Peaks" (ABC, 1990-91), its slightly demented tone was still an acquired taste for many viewers, and it struggled to find a following, finally catching fire its third season. The fan of "St. Elsewhere" (NBC, 1982-88) then created the medical drama "Chicago Hope" (CBS, 1994- ), which went toe-to-toe with ultimate ratings-winner "ER" (NBC, 1994- ), writing 40 one-hour episodes that season between his two shows, a Dickensian output that understandably left him burnt out. Turning over executive producing duties on both series the following season to spend more time with his family, he scripted only a few episodes. "Chicago Hope" managed to continue despite losing singing surgeon Mandy Patinkin and hospital legal counsel Peter MacNicol (who left because of Kelley's reduced role just as Harry Hamlin had departed "L.A. Law" when Kelley did in 1992), but "Picket Fences" could not survive Kelley's lack of involvement.

While on hiatus, Kelley co-produced and scripted "To Gillian on Her 37th Birthday" (1996, adapted from Michael Brady's play), a straightforward tearjerker starring his wife, Michelle Pfeiffer. Feature success, however, did not make him turn his back on the medium in which he had become established as one of the best dramatic writers ever. In March of 1997, he returned with "The Practice" (ABC), a much grittier and truer look at a law firm (this time in Boston) than the glitzy "L.A. Law", and the show limped along awhile on life support, overcoming its disastrous Saturday night time slot to win the Emmy as Outstanding Drama Series. In the fall, he also debuted "Ally McBeal" (1997- ), an immediate sensation because of its fun, hip, unconventional representation of a confused young lawyer (Calista Flockhart) who works alongside the lost love of her life in a big-fee Boston firm filled with other self-absorbed, mostly neurotic characters. Once again Kelley was writing practically all the episodes for two hour-long series by himself, but burnout did not set in as the two shows expressed different sides of the Kelley creativity (light and dark), each offering escape from the other. Most amazing of all, he had become the Michael Jordan of television while limiting himself to a 9-6 workday Monday through Friday.

If Kelley had been a step ahead of the zeitgeist with "Picket Fences", it had caught up to him for "Ally McBeal". Fantasy elements like the dancing baby, Ally's outrageously long tongue and the voice of Barry White that motivates John 'The Biscuit' Cage (MacNicol) captivated audiences almost immediately. Building on his use of music in "Chicago Hope", the writer-producer made it integral to the show, featuring Vonda Shepard's original songs and pleasant cover versions in every episode, as well as allowing almost every ensemble member a periodic vocal showcase. Though "The Practice" also addressed trademark Kelley issues of insecurity, failure and embarrassment, it was "Ally McBeal" that became the popular heavyweight, but Kelley himself envisions "The Practice" as the tortoise that may outlast the hare. He scripted two 1999 features, "Lake Placid" ("Jaws" meets "Fargo") and "Mystery, Alaska" ("Northern Exposure" meets "The Longest Yard"), which drew on his love of hockey, but the real story was that the 1999-2000 season found him at the control of five prime-time series. Not only had he resumed work on "Chicago Hope", but he had introduced the detective series "Snoops" (ABC, 1999- ) and "repurposed" previously aired episodes of "Ally McBeal" by cutting them to a half-hour format centered on the comedy storylines for Fox's "Ally" (1999-2002).

With the cancellation of "Ally" after its 2001-2002 run, Kelley wasted no time, promptly creating a new series to replace his immensely popular lawyer dramedy. "Girls Club" featured three single women working as lawyers in San Francisco.