“Crying all the way to the bank” (or “laughing all the way to the bank”) means that, regardless of the situtation, that person has made money to take to the bank. A critic once savagely reviewed the flamboyant pianist Liberace (1919-1987) in 1953, but the Liberace concert had been sold out. Liberace remarked that the review made him “laugh all the way to the bank.”
 
Citations of the phrase in 1946 and 1951 indicate that the phrase pre-dates Liberace’s use of it. Both citations involve the boxing business and the reaction of a losing fighter’s manager. Fights were often fixed and the loser was often guaranteed money, so a boxing loser could “cry all the way to the bank.” The 1951 citation mentions New York sports journalist and author Damon Runyon (1880-1946), and it is possible that he popularized the phrase. There is an isolated 1908 citation (below) of “laugh all the way to the bank.”
 
   
Wiktionary: laugh all the way to the bank
laugh all the way to the bank (third-person singular simple present laughs all the way to the bank, present participle laughing all the way to the bank, simple past and past participle laughed all the way to the bank)
1. (intransitive, idiomatic) To be happy due to the receipt of money.
   
Wiktionary: cry all the way to the bank
cry all the way to the bank
1. (idiomatic) To be happy due to the receipt of money, although expressing sorrow about the cause of such receipt.
When his rich aunt died, he was crying all the way to the bank.
   
The Free Dictionary
laughing all the way to the bank (informal)
if someone is laughing all the way to the bank, they have made a lot of money very easily, often because someone else has been stupid.
If we don’t take this opportunity, you can be sure our competitors will and they’ll be laughing all the way to the bank.
 
Wikipedia: Liberace
Wladziu Valentino Liberace (May 16, 1919 – February 4, 1987), better known by only his last name Liberace, was a famous American entertainer and pianist of Polish and Italian descent.
   
The Yale Book of Quotations
Edited by Fred R. SHapiro
New Haven, CT; Yale University Press
2006
Pg. 458:
Liberace (Wladziu Valentino Liberace)
U.S. entertainer, 1919-1987
“Thank you for your very amusing review. After reading it, in fact, my brother George and I laughed all the way to the bank.”
Quoted in TV Guide, 26 Feb.-4 Mar. 1954
   
Google Books
Peter
A novel of which he is not the hero
By F. Hopkinson Smith
New York, NY: Charles Scribner’s Sons
1908
Pg. 265:
Some of them heard Mason laugh all the way to the bank.
 
4 September 1946, Wisconsin State Journal (Madison, WI), Walter Winchell syndicated entertainment column, pg. 6, col. 6:
Eddie Walker perhaps is the wealthiest fight manager in the game…The other night when his man Belloise lost, Eddie had the miseries…He felt so terrible, he cried all the way to the bank!
 
28 January 1951, Amarillo (TX) News-Globe, “The Lyons’ Den” by Leonard Lyons, pg. 6G, col. 7:
Eddie Borden, the fight manager, heard Damon Runyon say it of another manager whose fighter had just been badly beaten and kayoed: “He felt miserable about it, and cried all the way to the bank.”
 
7 November 1953, San Mateo (CA) Times, pg. 3A, col. 2:
So There
Recently a Chicago music critic gave Liberace a pretty rough time. The critic kind of overlooked the fact that the pianist had enjoyed a sellout crowd.
 
After reading this bitter attack on the Liberace show, the famous Milwaukee piano player wrote to the critic. “My manager and I laughed all the way to the bank.”
   
Google News Archive
13 July 1954, Rome (GA) News-Tribune, pg. 4, col. 2:
When newspaper critics hooted his latest mincing performance, Liberace wired each of them (says Bennett Cerf): “Your cruel remarks made me so unhappy I cried all the way to the bank.”