6. The Cure for Insomnia
5,220 minutes (90 miles of film)
Video artist John Henry Timmis IV filmed his colleague, outsider artist Lee Groban, reading a four-thousand-page poem called “The Cure for Insomnia” in 1987. In the years since the filming, Groban continued to expand the poem until, by his death in 2011, it had reached 5,000 pages. Timmis himself was a local punk icon who always liked to record video along with his music — his legacy is mostly musical, besides his record-breaking entry in the 11 longest most meaningless movies in the world.