Complex sentence: It is shown the night Obree breaks the record he is prone to crippling bouts of depression, which is exacerbated when Boardman breaks the record and he meets up with one of his childhood bullies.
Split into simpler sentences: It is shown that on the night Obree breaks the record he is severely depressed. This is exacerbated when Boardman breaks the record and when Obree meets up with one of his childhood bullies.