The term “Wailing Wall Street” (Wailing Wall + Wall Street) is associated with the Wall Street Crash of 1929 and “Black Thursday” (October 24th), but printed citations appeared slightly earlier. “If the stock market does any morn funny business we’re in favor of calling it Wailing Wall Street” was cited on September 27th. “Recent stock market reverses lead to the suggestion that perhaps it ought to be renamed Wailing Wall Street” was cited on September 28th. “When market ‘breaks,’ it’s known as Wailing Wall Street” was cited on October 9th.
 
New York City-born entertainer Eddie Cantor (1892-1964) lost a fortune in October 1929 and wrote a book, Caught Short! A Saga of Wailing Wall Street (1929) by “A.C.” (After Crash).
 
 
Wikipedia: Wall Street
Wall Street is a 0.7-mile-long (1.1 km) street running eight blocks, roughly northwest to southeast, from Broadway to South Street on the East River in the Financial District of lower Manhattan, New York City.[2] Over time, the term has become a metonym for the financial markets of the United States as a whole, the American financial sector (even if financial firms are not physically located there), or signifying New York-based financial interests.
 
Anchored by Wall Street, New York City has been called both the most economically powerful city and the leading financial center of the world, and the city is home to the world’s two largest stock exchanges by total market capitalization, the New York Stock Exchange and NASDAQ. Several other major exchanges have or had headquarters in the Wall Street area, including the New York Mercantile Exchange, the New York Board of Trade, and the former American Stock Exchange.
 
Wikipedia: Western Wall
The Western Wall, Wailing Wall or Kotel (Hebrew: About this sound הַכֹּתֶל הַמַּעֲרָבִי (help·info), translit.: HaKotel HaMa’aravi; Ashkenazic pronunciation: Kosel; Arabic: حائط البراق‎, translit.: Ḥā‘iṭ Al-Burāq, translat.: The Buraq Wall) is located in the Old City of Jerusalem. It is a relatively small western segment of the walls surrounding the area called the Temple Mount (or Har Habayit) by Jews, Christians and most Western sources, and known to Muslims as the Noble Sanctuary (Al-Haram ash-Sharīf).
 
The Temple Mount is the holiest site in Judaism and is the place to which Jews turn during prayer.
   
Wikipedia: Eddie Cantor
Eddie Cantor (c. January 31, 1892 – October 10, 1964), born Edward Israel Iskowitz, was an American “illustrated song” performer, comedian, dancer, singer, actor and songwriter. Familiar to Broadway, radio, movie and early television audiences, this “Apostle of Pep” was regarded almost as a family member by millions because his top-rated radio shows revealed intimate stories and amusing anecdotes about his wife Ida and five daughters.
(...)
Cantor was one of the era’s most successful entertainers, but the 1929 stock market crash took away his multi-millionaire status and left him deeply in debt. However, Cantor’s relentless attention to his own earnings in order to avoid the poverty he knew growing up caused him to use his writing talent, quickly building a new bank account with his highly popular, bestselling books of humor and cartoons about his experience, Caught Short! A Saga of Wailing Wall Street in 1929 “A.C.” (After Crash), and Yoo-Hoo, Prosperity!
 
27 September 1929, The Daily News Standard (Uniontown, PA), pg. 4, col. 1:
If the stock market does any morn funny business we’re in favor of calling it Wailing Wall Street.
 
28 September 1929, Syracuse (NY) Herald, “Barbs,” pg. 4, col. 7:
Recent stock market reverses lead to the suggestion that perhaps it ought to be renamed Wailing Wall Street.
     
9 October 1929, Rockford (IL) Register-Gazette, “Bo Broadway” by Joseph Van Raalte (By Central Press), pg. 6, col. 7:
TODAY’S FUN
When market “breaks,” it’s known as Wailing Wall Street.
 
5 November 1929, Quanah (TX) Tribune-Chief, pg. 5, col. 2:
Every time there is an advance in the rate of call loans, New York has its Wailing Wall Street.—Philadelphia Inquirer.
 
OCLC WorldCat record
Caught short! : a saga of wailing Wall Street
Author: Eddie Cantor
Publisher: New York : Simon and Schuster, 1929.
Edition/Format:   Print book : English
 
OCLC WorldCat record
Is Jesse James the father of Wall Street? Or “Mentally chloroformed and legally robbed in wailing Wall Street.”
Author: Ima Lamb, pseud.
Publisher: San Francisco [193-?]
Edition/Format:   Print book : English
 
Google Books
Esquire
Volume 2, Issues 4-7
1934
Pg. 98:
The nature of their work being especially adapted to concocting clever names for places, they have divided their own “Noo Yawk” into the Stem, the (Main) Drag, the Artery, Maraudway, the Milky Way, the Galaxy, the Gay White Way, the Dirty White Way, the Big or Main Alley, the Grandest Canyon, the Glittering Stem, Mazda Lane, Neon Boulevard, the (Big) Gulch, Gin Gulch, the Noisy Lane, the Street, Wailing Wall Street, the (Grand) Canyon, the Golden Canyon, Hard Times Square, Pokahvenoo, the Roaring Forties, the Naughty Nineties, Mad-hattan, etc., etc.
 
Google Books
High Steppers, Fallen Angels, and Lollipops:
Wall Street Slang
By Kathleen Odean
New York, NY: Dodd, Mead
1988.
Pg. 143:
But, in contrast to Merrill’s positive use of Wall Street as a metaphor, comedian Will Rogers sided with those who dubbed it Wailing Wall Street: ...
 
OCLC WorldCat record
Investment banking Wailing Wall Street
Edition/Format: Article Article : English
Publication: ECONOMIST -LONDON- ECONOMIST- (October 5, 2002): 13
Database: British Library Serials