Lord of the Rings was boring at the start and peaked out on boringness during the Tom Bombadil part. I had to restart about 3 times (with about a year's gap in between) jsut to get past that bit.
My answer is probably The Turn of the Screw by Henry James. It was short but took me bloody age to...
On my first lesson I stalled no fewer than 9 times at a roundabout. The driver behind me obviously believed that I was doing it on purpose and that beeping his horn was the only way to help.
On my second lesson I flipped the car onto its roof while doing a three point turn.
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