"That’s the way the cookie crumbles” (also “that’s how the cookie crumbles") means that even a good thing (a cookie) sometimes breaks apart. A similar expression accounting for unfortunate events is “That’s life!”
“That’s the way the cookie crumbles” is cited in print from March 1955 and quickly became a part of the slang expressions of American teenagers. The “cookie” expression is dated and is infrequently used today.
The Free Dictionary
That’s the way the cookie crumbles. (British, American & Australian, informal, American, informal)
something that you say which means that bad things sometimes happen and there is nothing you can do to prevent it, so it is not worth becoming upset about it.
I can’t believe they chose Sam for the job and not me. Ah well, that’s the way the cookie crumbles.
(Oxford English Dictionary)
Colloq. phr. (chiefly U.S.): (that’s) how (or the way) the cookie crumbles, (that is) how the position resolves itself; that is the way it is.
1957 Sat. Even. Post 7 Sept. 59 From then on, that’s the way the cooky crumbled. I enjoyed having good ratings, but I didn’t enjoy the viciousness of the railbirds’ thrusts at Berle.
1959 WENZELL BROWN Cry Kill iv. 45 No matter how the cookie crumbled, Mamma Ida was in for a bad time.
1961 WODEHOUSE Ice in Bedroom v. 40 Oh well, that’s the way the cookie crumbles. You can’t win ‘em all.
1964 Listener 16 Apr. 612/2 We shall not know how, as the Americans say, the cookie crumbles.
3 March 1955, Uniontown (PA) Evening Standard, “The Junior Reporter Club,” pg. 27, col. 2:
Well that’s the way the cookie crumbles.
27 November 1955, Helena (MT) Independent Record, “Freckles and His Friends” comic, pg. 47:
SORRY, DAD, BUT THAT’S THE WAY THE COOKIE CRUMBLES.
29 March 1956, Mexia (TX) Daily News, pg. 10, col. 1:
“Oh well, that’s how the cookie crumbles.”
13 August 1956, Portsmouth (OH) Times, pg. 22, col. 1:
THAT’S THE WAY the cookie crumbles.
24 August 1956, Long Beach (CA) Independent, pg. 2, col. 1:
WELL, THAT’S when the cookie crumbled, right there.
10 October 1958, New York (NY) Times, pg. 38:
“But,” he said, using a common among baseball players, “that’s the way the cookie crumbles and that’s the way the ball bounces.”
5 March 1959, Washington (DC) Post, “Cookie Record Crumbles,” pg. C11:
“THAT’S the way the cookie crumbles”—a slang phrase favored by teen-agers --has special meaning for a pair of Fairfax County Girl Scouts.
The Zoo Story: The Death of Bessie Smith; The Sandbox; Three Plays
By Edward Albee
New York, NY: Coward-McCann
JERRY (Lightly mocking) But that’s the way the cookie crumbles?
New York City • Food/Drink • (0) Comments • Tuesday, January 27, 2009 • Permalink