“Like nailing jelly to the wall” (“Like nailing jello to the wall”)
“Like nailing jelly to the wall” means something difficult-to-impossible. Theodore Roosevelt (1858-1919) coined the expression in April 1912:
“Somebody asked me why I did not get an agreement with Colombia. They might just as well ask me why I do not nail cranberry jelly to the wall. It would not be my fault or the fault of the nail, it would be the fault of the jelly.”
“Nail jello to the wall” has been cited since at least 1955 and “nail jello to a tree” since 1962. Historian William B. Hesseltine wrote a widely cited version in 1945: ““Writing intellectual history is like trying to nail jelly to the wall.”
The Free Dictionary
like nailing jelly to the wall
if something is like nailing jelly to the wall, it is impossible to understand or describe it exactly Writing a history of the period is like nailing jelly to the wall.
Wikipedia: Theodore Roosevelt
Theodore “Teddy” Roosevelt (pronounced /ˈroʊzəvɛlt/ ROE-zə-velt; October 27, 1858 – January 6, 1919) was the 26th President of the United States. He is noted for his energetic personality, range of interests and achievements, leadership of the Progressive Movement, and his “cowboy” image and robust masculinity. He was a leader of the Republican Party and founder of the short-lived Progressive (“Bull Moose”) Party of 1912. Before becoming President (1901–1909) he held offices at the municipal, state, and federal level of government. Roosevelt’s achievements as a naturalist, explorer, hunter, author, and soldier are as much a part of his fame as any office he held as a politician.
Wikipedia: Jell-O
Jell-O is a brand name belonging to U.S.-based Kraft Foods for a number of gelatin desserts, including fruit gels, puddings and no-bake cream pies. The brand’s popularity has led to it being used as a generic term for gelatin dessert across the U.S. and Canada.
Newspapers.com
8 April 1912, Tacoma (WA) Daily News, pg. 7, col. 3:
COLONEL COULDN’T NAIL JELLY TO THE WALL
Delivers Metaphor on Colombia—Attacks McKinley in Home District.
DECATUR, Ill., April 8.—In the district of Congressman McKinley, manager of President Taft’s campaign, Col. Roosevelt today took the cudgel against the Congressman. The first of his six speeches was made at Clinton, where he said:
(...)
Laughter greeted a new metaphor the colonel made while speaking of Panama.
“Somebody asked me why I did not get an agreement with Colombia. They might just as well ask me why I do not nail cranberry jelly to the wall, it would not be my fault or the fault of the nail; it would be the fault of the jelly.”
Google News Archive
9 April 1912, Boston (MA) Evening Transcript, “Roosevelt Hat Stays In,” pg. 2, col. 3:
Fort Wayne, Ind, April 9—Colonel Theodore Roosevelt said last night that if he was beaten in the present fight he would make another one.
(...)
The colonel brought out a shout of laughter when he introduced a new figure of speech. Speaking of the canal, he said: “Somebody asked me why I did not get an agreement with Colombia. They might just as well ask me why I do not nail cranberry jelly to the wall. It would not be my fault or the fault of the nail, it would be the fault of the jelly.”
9 April 1912, New York (NY) Times, pg. 1:
“Somebody asked me why I (Theodore Roosevelt—ed.) did not get an agreement with Colombia. They might just as well ask me why I do not nail cranberry jelly to the wall. It would not be my fault or the fault of the nail; it would be the fault of the jelly.”
Google News Archive
4 February 1928, Border Cities Star (Windsor, Ontario), “Ottawa” by R. J. Deachman, pg. 16, col. 6:
Mr. King answered Mr. Bennett, but the premier was not at his best. Nailing jelly to the wall, is not a simple task.
Newspapers.com
11 June 1955, Ottawa (Ontario) Journal, “Saving Millions Isn’t Everything” by James M. Minifie, pg. 2, col. 1:
For the experience of the Commission was that saving money was rather like trying to nail jello to the wall.
Google Books
Christianity and the Scientist
By Ian G. Barbour
New York, NY: Association Press
1960
Pg. 112:
Trying to pin some people down to a definite position on any subject is like trying to nail jello to the wall.
21 October 1962, Pasadena (CA) Independent Star-News, “Capital Chatter,” pg. 10, col. 5:
Phrases for the Congo
Clare H. Timberlake, former Ambassador to the Congo, has a couple of neat phrases to describe the situation in that embattled country. Describing how it felt to try to bring order out of the Congolese chaos, Timberlake said: “It’s like trying to nail jello to a tree.”
Google News Archive
29 September 1963, Pittsburgh (PA) Press, TV Graphic, pg. 4, col. 1:
GETTING facts from Swedish-born Inger Stevens during a luncheon interview is like trying to nail jello to the wall.