Horrible Bosses Movies in Order Film series·2011–2014 2 films from 2011 to 2014, 3 hours of viewing in all. In order 1 Horrible Bosses 2011 1 hr 38 min Directed by Seth Gordon Rent or buy DVD & Blu-ray 2 Horrible Bosses 2 2014 1 hr 44 min Directed by Sean Anders Rent or buy DVD & Blu-ray Film data from Wikidata.