Goodbye, Mr. Blackwell: Sometimes Tough Love Is The Best Kind.

One of fashion’s most controversial figures, the cantankerous Mr. Blackwell, died early this week at the age of 86. Interestingly, his sudden void may help revise his trenchant reputation — one he perhaps didn’t fully deserve. For in those arch, annual Worst Dressed Celebrities Lists that we hated to love, there was brutally honest advice for the style victims the curmudgeonly fashion critic loved to hate.

Famously impertinent, Blackwell long ago established a familiar entertainment niche; now, the public mocking of ill-advised celebrity fashion choices is practically a global pasttime. While hardly qualifying as high art itself, his sneering disdain debunked the odious conceits of celebrity styling, and encouraged skeptical candor towards celebrity. Call it a public service, if you will.

He was hardly the cuddliest of figures, but Mr. Blackwell’s sardonic tokens of tough love will, oddly, be missed. The inexpert cruelties of the Perez Hilton set embody the new generation of celebrity-baiting slander. Where Blackwell’s jeers pierced egos to improve wardrobes, their intentions border on mean-spirited career homocide. Theirs is a heartless, pitiful caricature of Blackwell’s legacy.

After all, it is indeed a rich, snarky, and specific tradition to uphold. Casualties of Blackwell’s Worst Dressed list have run the gamut of bold print names. Among his famously scorned: Madonna, who he dubbed “the great bare-bottomed bore of Babylon”, and her protégé Britney Spears (“her bra-topped collection of Madonna rejects are pure fashion overkill”).

Blackwell’s style offenders have also included Patty Davis, who “packs all the glamour of an old, worn out sneaker”, and Lindsay Lohan (“from adorable to deplorable”).

Such comments betray the biting, but harmless humor of Blackwell. He was mischievous, not mean. Blackwell even admitted that often the most criticized of his Worst Dressed were people were those he greatly admired for their talent.

“The list is and was a satirical look at the fashion flops of the year,” he said in 1998. “I merely said out loud what others were whispering. … It’s not my intention to hurt the feelings of these people. It’s to put down the clothing they’re wearing.”

Rest in Peace, Mr. Blackwell. Even your worst-dressed knew your black humor wasn’t without heart.

In tribute, here are more of Blackwell’s infamous japes on celebrity styling misadventures. Feel free to add your own.

Barbra Streisand: “She looks like a masculine Bride of Frankenstein.”

Christina Aguilera: “A dazzling singer who puts good taste through the wardrobe wringer.”

Meryl Streep:
“She looks like a gypsy abandoned by a caravan.”

Sharon Stone: “An over-the-hill Cruella DeVille.”

“A Hells Angel escapee who invaded the Ziegfeld Follies on a rainy night.”

Camilla Parker-Bowles: “The Duchess of Dowdy.”

Bjork: “She dances in the dark — and dresses there, too.”