"Loop-the-Loop" is the name of a new entertainment which goes further in the way of tempting Providence than anything yet invented. The "Loop" is an immense circle of track in the air. A car on a mimic railway shoots down a very steep incline, and is impelled around the inner side of this loop. ... The authorities at Coney Island are said to have prohibited "looping-the-loop" because women break their corset strings in their efforts to catch their breath as they sweep down the incline, and moreover, a young man is reported to have ruptured a blood vessel in his liver. ["Philadelphia Medical Journal," Aug. 10, 1901]
You can reason with a bull dog, astonish a bull, fascinate a boa, frighten a tiger, soften a lion; no resource with such a monster as a loose cannon. You cannot kill it, it is dead; and at the same time it lives. It lives with a sinister life which comes from the infinite. It is moved by the ship, which is moved by the sea, which is moved by the wind. This exterminator is a plaything. [Victor Hugo, "Ninety Three"]
Loose end in reference to something unfinished, undecided, unguarded is from 1540s; to be at loose ends is from 1807. Phrase on the loose "free, unrestrained" is from 1749 (upon the loose).