The phrase to laugh—also to cry—all the way to the bank means to relish—also (ironically) to deplore—the fact that one is making money, especially undeservedly or at the expense of others.

This phrase is first recorded in Peter: A Novel of Which He is Not the Hero (New York: Charles Scribner’s Sons, 1908), set in New York City’s financial world, by the American author, artist and engineer Francis Hopkinson Smith (1838-1915):

The second Mukton Lode scoop,—the one so deftly handled the night of Arthur Breen’s dinner to the directors,—had somehow struck a snag in the scooping with the result that most of the “scoopings” had been spilled over the edge there to be gathered up by the gamins of the Street, instead of being hived in the strong boxes of the scoopers. Some of the habitues in the orchestra chairs in Breen’s office had cursed loud and deep when they saw their margins melt away; and one or two of the directors had broken out into open revolt, charging Breen with the fiasco, but most of the others had held their peace. It was better to crawl away into the tall grass there to nurse their wounds than to give the enemy a list of the killed and wounded. Now and then an outsider—one who had watched the battle from afar—saw more of the fight than the contestants themselves. Among these was Garry Minott.
“You heard how Mason, the Chicago man, euchred the Mukton gang, didn’t you?” he had shouted to a friend one night at the Magnolia—“Oh, listen! boys. They set up a job on him,—he’s a countryman, you know a poor little countryman—from a small village called Chicago—he’s got three millions, remember, all in hard cash. Nice, quiet motherly old gentleman is Mr. Mason—butter wouldn’t melt in his mouth. Went into Mukton with every dollar he had—so kind of Mr. Breen to let him in—yes, put him down for 2,000 shares more. Then Breen & Co. began to hoist her up—five points—ten points—twenty points. At the end of the week they had, without knowing it, bought every share of Mason’s stock.” Here Garry roared, as did the others within hearing. “And they’ve got it yet. Next day the bottom dropped out. Some of them heard Mason laugh all the way to the bank. He’s cleaned up half a million and gone back home—‘so afraid his mother would spank him for being out late o’ nights without his nurse.’”

The earliest occurrence of the phrase that I have found is from the gossip column On Broadway, by the American journalist Walter Winchell (a.k.a. “Man About Town” – 1897-1972), published in many American newspapers in September 1946—for example on Monday 2^nd in the Newark Star-Ledger (Newark, New Jersey):

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!

The context of the second-earliest instance of the phrase that I have found is very similar to that of the preceding quotation: to cry all the way to the bank was also used about a fight manager whose boxer had been beaten; this appeared in the column The Lyons Den, by Leonard Lyons, published in several newspapers on Friday 26^th January 1951—for example in the Pittsburgh Post-Gazette (Pittsburgh, Pennsylvania):

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.”

The phrase is especially associated with the popular American pianist and entertainer Władziu Valentino Liberace (1919-87), who was much derided by his critics for vulgarity and lack of talent. In From ‘B’ Pictures to Top TV Stardom, published in the San Mateo Times (San Mateo, California) of Saturday 7^th November 1953, Bob Foster wrote the following:

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 the critic. “My manager and I laughed all the way to the bank.”

Likewise, this is from David Felt’s Column, in the Southern Illinoisan (Carbondale, Illinois) of Friday 2^nd July 1954:

The story is not new and you may have heard it, but we repeat it here in the interest of good sportsmanship and fair play.
Liberace—you know, that fellow who plays the piano—seems to be able to answer the music critics who are practically 100 per cent against him.
Bennet Cerf tells it this way:
When reviewers on the major New York newspapers hooted derisively at his Madison Square Garden performance (packed to the rafters with palpitating females), Liberace wired each and every detractor:
“Your cruel remarks made me so unhappy I cried all the way to the bank.”

Władziu Valentino Liberace’s brother, the American musician and television performer George Liberace (1911-83), is said to have also used the phrase to reply to critics. For example, the following is from The Times-Picayune (New Orleans, Louisiana) of Saturday 27^th March 1954:

George Liberace, a chubby-cheeked, mustached violinist-maracas player, conducted his orchestra with smiling aplomb in concert Friday night at Municipal Auditorium before a huge and exceedingly demonstrative audience.
[…]
The first pianist made comment about certain critical reviews the group has received and confided, with a smile, that “George read the articles and cried all the way to the bank.”

And, in Liberace Enthralls Picture-Taking Fans, published in The Detroit Free Press (Detroit, Michigan) of Friday 7^th May 1954, Riley Murray wrote this about a concert given the previous day by Władziu Valentino Liberace:

Liberace first introduced his musician associates, including his brother, George.
[…]
He launched into an attack on Free Press columnist John Crosby, who had criticized his pianistic efforts.
He repeated his crack that when his brother read Crosby’s insults, he “cried all the way to the bank.”