Orr is a World War II bomber pilot who shares a tent with his good friend, the protagonist of the novel, Yossarian.
His most notable feature is repeatedly being shot down over water, but, until his final flight, always managing to survive along with his entire crew.
Only in the last ten pages of the novel does Heller reveal that Orr's crashes were part of an elaborate (and successful) plot to escape the war.
When this fails, Orr plans to ditch in the sea and make his way to a neutral country where he can wait out the war.
Orr practices this second goal by getting shot down every mission he flies, and so becomes an expert in ditching, without losing a single crewman.
Orr is good friends with Yossarian and enjoys winding him up with his stories of crabapples and horse-chestnuts or about the prostitute that kept hitting him over the head.
However, he is eventually revealed to have had the clearest view of the absurdities of their situation through his carefully planned escape to Sweden.
Orr has a bucktoothed smile and frequently puts crabapples or horse chestnuts in his cheeks and rubber balls in his hands.
Orr never gives any straightforward explanation for this other than he wants big cheeks and to detract from the peculiarity of this he keeps rubber balls in his hands.
The vicious cycle ends after fifteen to twenty minutes when she knocks him out cold with a good whack to his head, leaving him with a concussion "that kept him out of combat for only twelve days."
At first, his frequent airplane crashes[5] seems to hint toward a clumsy, foolish pilot who has little knack and knowledge for his craft.
The generals, colonels, and other commanding officers in the higher echelons constantly and consistently appear to be vain and care only about their own careers.
Throughout the last ten chapters Yossarian along with Orr thinks diligently about crashing near a neutral country such as Switzerland or Sweden[6] to be interned there for the rest of the war.
Since heading directly toward one of the two countries would give the appearance of fleeing similar to AWOL, a more surreptitious and clandestine indirect path would work better.
[5] He used the crashes as practice for ocean survival techniques, as is evident when he and his crew members are in a life raft.
The news of this escape eventually reaches Yossarian while he is in hospital, causing him to undergo a revelation as to Orr's motives about his actions and re-energizes him to keep on "fighting the system".