The 40ft diameter ribbon drag chute used on the Space Shuttles was pretty impressive. It was added as a safety measure after the Challenger accident. The drag chute was deployed routinely on every landing, but I believe it was used more for directional stability than for braking. The Orbiter's un-powered landing was difficult under the best of conditions. The MLG tire treads were worn thru during landing and had to be replaced after every mission.
Here's an interesting paper on the Orbiter drag chute:
http://www.coengineers.com/wp-conten...2013009780.pdf