“In honor of tax season, for an extra $50, the hookers in Times Square will handle your extension”

American late night television comedian David Letterman hosted the New York City-based shows Late Night with David Letterman on NBC and Late Show with David Letterman on CBS, broadcasting from 1982 to 2015. He often told jokes about Times Square hookers, even though the joke really belonged in the 1970s, before Times Square was cleaned up. In April just before the tax deadline, he often told this joke:
 
”In honor of tax season, for an extra $50, the hookers in Times Square will handle your extension.”
 
The joke was told in 1999, 2003 and 2005, and possibly in other years as well. The joke is popular every April, but tellers of the joke have sometimes changed “Times Square” to other seedy locations.
   
   
Wikipedia: David Letterman
David Michael Letterman (born April 12, 1947) is an American former television and radio host, comedian, writer, producer, and actor.
 
He hosted a late night television talk show for 33 years, beginning with the February 1, 1982, debut of Late Night with David Letterman on NBC, and ending with the May 20, 2015, broadcast of the Late Show with David Letterman on CBS. In total, Letterman hosted 6,028 episodes of Late Night and Late Show, surpassing friend and mentor Johnny Carson as the longest-serving late night talk show host in American television history. In 1996, Letterman was ranked No. 45 on TV Guide‘s 50 Greatest TV Stars of All Time.
         
Entertainment Weekly
Sound Bites: The week’s best TV Quotes
TV’s funniest lines from April 24 to 30
BY EW STAFF
Posted April 30 1999 — 12:00 AM EDT
(...)
”In honor of tax season, for an extra $50, the hookers in Times Square will handle your extension.”
David Letterman on Late Show
 
Google Books
The Reader
By Bifford Debs
Lincoln, NE: iUniverse, Inc.
2002
Pg. 135:
In case you didn’t catch his Late Show just before April fifteen, Letterman likened prostitutes to tax accountants when he said they would ‘handle your extension’ for a certain fee.
 
Google Groups: alt.fan.letterman
Tues 4/15 Big Show Synopsis
Brady
4/16/03
Ya know, I really don’t mind paying taxes. I just wish Congress would ...
Oh, forget it. Here’s how I saw last night’s show ...
 
Monologue ... I don’t remember much about last night’s monologue. I *do* remember the last joke, which I enjoyed. (“Once again, the hookers in Times Square are offering their tax deadline special—for an extra 50 bucks, they’ll handle your extension.”) I have a confession. I may not have remembered that joke if not for the fact that MikeMack highlighted it in today’s ‘Wahoo.’ But I really did enjoy it.
     
Google Groups: alt.fan.letterman
Wed. 4/13 Big Show Synopsis
Brady
4/14/05
(...)
“But here’s good news for you late [income tax] filers. The hookers in Times Square—bless their hearts—[are] offering their annual tax deadline special. (anticipatory laughter) Their tax deadline special. For an extra fifty bucks, they’ll handle your extension.”
 
Google Groups: alt.fan.letterman
Dave’s “Hookers In Times Square” Jokes
Phone the Kids, Wake the Neighbors
7/7/06
I wonder how many different “Hookers In Times Square” jokes Dave has told over the years…
 
“In honor of the US Open, the hookers in Times Square are offering their John McEnroe special. For $50, they’ll tell you it was in.”
 
“Today is April 15, so the hookers in Times Square are offering their Tax Day Special. For an extra $10, they’ll handle your extension.”
   
Google Books
Stop Me If You’ve Heard This:
A History and Philosophy of Jokes
By Jim Holt
New York, NY: W. W. Norton & Company, Inc.
2008
Pg. 79:
Or the one about how Times Square hookers get into the tax-season spirit around April 15: For an extra fifty dollars they’ll handle your extension.
 
Twitter
Mick Conwah
‏@mickers79
Tax time again…for an extra $50, the hookers on Wenthworth Ave will handle your extension.
2:24 PM - 21 Jan 2011
 
Twitter
Joe Hayes
‏@mdvaldosta
IRS blues? The hookers in downtown Valdosta are offering an income tax special. For $25 they will handle your extension.
1:15 PM - 2 Apr 2012
 
Twitter
Shirl Sultzbach
‏@yesiam27
It’s tax time and the hookers in New York would be happy to handle your extension for an extra 50 bucks!
9:29 AM - 14 Apr 2014
Pennsylvania, USA