Tuckerman Ravine on Mount Washington is about as legendary of a ski area as they come, being a bucket list item for many East Coast skiers and snowboarders. Its difficulty, usual less-than-ideal conditions, and more remote location mean that airs are fairly rare, but they do happen.
Jamie Pierre is widely regarded as holding the world record highest ski cliff jump at 255 feet set in 2006 in the backcountry of Grand Targhee, Wyoming. Jamie's leap was 100% deliberate but there is another skier who unintentionally sent a larger cliff and his record is somewhat disputed around the ski world.
There are a lot of difficult and iconic ski runs in the world, from Jackson Hole's Corbet's Couloir to the impossibly steep Streif at Kitzbühel. But when combining steep slopes with massive moguls, nothing in Europe can compare to The Swiss Wall at Les Portes du Soleil. Starting from Avoriaz in France and ending in Les Crosets in Switzerland, the Swiss Wall is often considered one of, if not the, most difficult on-piste slopes in Europe.