Complex sentence: His interventions in the comic strips often consist of him trying to cheer up Migraine Boy, most frequently by trying to play games with him (usually dress-up ones), or trying to find ways to relieve him from his headache.
Split into simpler sentences: His interventions in the comic strips often consist of him trying to cheer up Migraine Boy. The most usual ways to do this are trying to play games with him, usually dress-up ones, or trying to find ways to relieve him from his headache.