“How’s the weather up there?” is a jocular line said to a very tall person. “How’s the weather up there?” has been cited in print since at least 1886—when a “six-foot-two-ter” was considered tall. The question was called a stock phrase by 1901.
   
Circus giant Jack Earle said in 1950 that the question annoyed him and had been asked at least 10,000 times.
 
“This guy was so large, he had his own climate” is a similar saying. “What do you say to a leprechaun?”/“How’s the weather down there?” is a related riddle.
   
 
Chronicling America
8 December 1886, Hartford (KY) Weekly Herald, “Scientific,” pg. 3, col. 5:
Little Medford Howard met a six-foot-two-ter on the street the other day, and thus accosted him: “Stranger, hand me down a chaw of store tobacco. Thanks. How’s the weather up there?”
 
9 December 1901, Boston (MA) Herald, “Probably the Tallest Woman,” pg. 10, cols. 4-5:
“No, I don’t mind being questioned now, but some people make me awfully tired—those who ask me all about my life from babyhood, besides, of course, all the stock phrases that are usually applied to anyone of unusual stature, such as ‘How’s the weather up there?’ etc.”
 
Google News Archive
25 April 1934, The Deseret News (Salt Lake City, UT), pg. 9, col. 5 photo caption:
How’s The Weather Up There?
Introducing Sheriff Lou Boedecker (right) of Deer Lodge, Montana—the biggest sheriff in America—to Gov. Henry H. BLood at the capitol today. Sheriff Boedecker, though he stands six feet seven inches tall and weighs 272 pounds, looks like a small man so well proportioned is he.
 
Google News Archive
4 February 1935, Sarasota (FL) Herald, pg. 5, col. 5 photo caption:
‘HOW’S THE WEATHER UP THERE?’
That, or something like it, is what Jimmy Angelich, star football and basketball player at the University of Alabama, is saying to “Shorty” SNeed, substitute center on the basketball team. “Shorty” stands six feet, seven inches without benefit of socks, just 11 inches taller than Jimmy.
 
Google News Archive
10 June 1935, Milwaukee (WI) Journal, sec. 2, pg. 1 photo caption:
‘How’s the Weather Up There?’
BETWEEN 350 and 400 Boy Scouts of the north district participated in a field meet Sunday afternoon in Lincoln park where they exhibited sout work. These seven bys of Troop 77 demonstrated their ability to form a human pyramid.
 
Google News Archive
16 May 1950, Spokane (WA) Daily Chronicle, pg. 17, col. 1:
Old ‘How’s the Weather’ Gag Worst, Says Ex-Circus Giant
By HAL BOYLE
NEW YORK, May 16. (AP)—The thing that Jack Earle hated most about being a circus giant was having people ask, “How’s the weather up there?”
 
“I figure I was asked that question at least 10,000 times,” recalled Earle.
 
Google News Archive
14 May 1960, Lawrence (KS) Daily Journal, pg. 1, col. 4 photo caption:
How’s the Weather Up There?
For little Tootsie, a Manchester terrier owned by Mrs. James Hattabaugh of 1417 E. 15th St., it’s a bit hard to believe that any other canine could come in a size like that of this Great Dane.
   
Google News Archive
1 October 1956, Deseret News and Telegram (Salt Lake City, UT), “Daily Children’s Story” by Mabel Harmer, pg 10B, cols. 1-2:
An elephant in the lot across the way strolled over to the fence and called, “Hi, Penelope! and I do mean high Penelope (a giraffe—ed.). How’s the weather up there?”
 
Penelope turned her head with what dignity she could muster. “You see,” she said, “if I hear it once I hear it twenty times a day. ‘How’s the weather up there?’ Sometimes I wish I was an ostrich and could hide my head.”
 
Sports Illustrated
December 05, 1966
‘LEWIE IS A MINORITY OF ONE’
By Frank Deford
(...)
Alcindor, who is 7 feet 1 inch, is, in fact, only slightly taller than 50 collegians who are in the neighborhood of 7 feet. (Brigham Young has three.)
(...)
“You’ve heard them all: ‘Watch your head.’ ‘How’s the weather up there?’ ‘You must have trouble sleeping.’ All that. The one I hear most now”—here Alcindor looks up—“is ‘Boy, and I thought I was tall.’”
 
New York (NY) Times
SPORTS OF THE TIMES; When Some Wondered If Lew Had It
By Ira Berkow
Published: April 22, 1989
(...)
Pavalon recalled that he had spent a day with the young Alcindor and ‘‘everywhere we went people were asking him, ‘How’s the weather up there?’ and stuff like that.’‘
 
Google Books
Title Hey Mrs. Longdrinkofwater: How’s the Weather Up There?
Author Barbara A. Berman
Publisher Xlibris Corporation, 2003
ISBN 1401099416, 9781401099411
Length 24 pages