Based on the clue 'at 19 this country cutie became the youngest singe...', what is the answer?

What is associated with: at 1815 feet it gives toronto some of the clearest tv reception in north america? What is associated with: at 183 miles wide 13000 feet deep bailly is the largest distinct one of these? What is associated with: at 1864 square miles its much bigger than its neighbor tobago? Based on the clue 'at 19 he was the youngest competitor in the house ...', what is the answer? What is associated with: at 1921s shuffle along you could sing along with eubie blake noble sissles im just wild about… What is associated with: at 1997s ceremony the first in the halls home city this rolling stone magazine founder said ic… What is associated with: at 1999s end this internet bookseller had seen its stock rise 6000 without showing a profit? Based on the clue 'at 1st only 1 appeared in a tragedy until aeschylu...', what is the answer?