"Master Chief Sucks at Escaping Prison" is the first episode of season 2.
An opening crawl that recaps the series so far kicks off the season, but it is too fast to be readable. Master Chief tells the Arbiter to slow it down. Afterwords, Master Chief gives advice on how to live in and escape from prison. He tells the viewer not to "drop the soap" and that they should violently attack other inmates if given any trouble. Finally, he encourages the viewer to start a riot in order to escape. On his way out, he and a prison guard have a Pokemon battle, and Master Chief wins. He encounters Tom Cruise guarding the Arbiter's cell. The Arbiter asks to stay behind as he has a plan. Master Chief agrees and leaves. After the credits, Cortana is shown telling Obama that she informed Master Chief of his destiny.
- Main character the King does not appear in this episode.
- The full trailer for the season involves Cortana saying that the prophecy describes the one who will defeat the King as an armored hero with little intelligence. However, as revealed later, there is no prophecy; instead a time travelling Master Chief directly tells Cortana he, specifically, is supposed to kill the King. Additionally, the King's dialogue in the trailer suggests he intends to destroy the world, which, as revealed at the end of the season, is untrue. None of the dialogue in the trailer appears in any episode.
- When Master Chief explains how to deal with unruly prisoners, he suggests "shoving their head up their ass" (a reference to Hancock) or throwing cooking fat in their face (a reference to Watchmen).
- When Master Chief suggests using his one phone call, the Joker is shown, referencing a scene from The Dark Knight. The person Master Chief calls is George Costanza (from a Seinfeld episode, "The Susie"), and George's famous answering machine picks up instead.
- Master Chief tells Tom Cruise to "literally fuck his own face," and Tom Cruise says "that's my line!," as that line is spoken by Cruise's character in Tropic Thunder.
- Master Chief has a Pokemon battle with the prison guard.
- The events of the previous episodes are recapped in the opening crawl. ("Master Chief: The Finale") ("Minisodes")
|<< S1 • << Mini||Master Chief Sucks at Ordering Season 2||MtA >> • S3 >>|
|Episode 1||"Master Chief Sucks at Escaping Prison"||September 1, 2008||Episode 5||"Master Chief Sucks at Time Travel"||February 13, 2009||Episode 10||"Master Chief Sucks at Remakes 2"||May 8, 2009|
|Movie||"Master Chief: The Movie (Parts 1 & 2)"||October 3, 2008||Episode 6||"Master Chief Sucks at Constants"||February 27, 2009||Episode 11||"Master Chief: The Second Finale (Part 1)"||May 13, 2009|
|Episode 2||"Master Chief Sucks at Voting"||November 4, 2008||Episode 7||"Master Chief Sucks at Super Smash Bros."||March 10, 2009||Episode 12||"Master Chief: The Second Finale (Part 2)"||May 13, 2009|
|Episode 3||"Master Chief Meets the Network"||November 22, 2008||Episode 8||"Master Chief Sucks at Computers"||March 23, 2009|
|Episode 4||"Master Chief vs the Superweapon"||January 17, 2009||Episode 9||"Master Chief vs Hillary Clinton"||April 20, 2009|