“Real barrel of laughs” (someone/something not funny)

An entertainment is sometimes said to be “a barrel of laughs” (to have a lot of laughs) or “a barrel of fun” (to have a lot of fun). The “barrel” term was popular in the 1800s and is still sometimes used today.
 
“Barrels of fun” was printed in the Manhattan (KS) Independent on May 19, 1866. “Barrel of fun” was printed in the New York (NY) Clipper on October 8, 1870, in a piece written by “Oofty Gooft,” a German dialect character of Augustus (Gus) Phillips.
 
“It contains a whole barrel of laughs and they are judiciously distributed” was said of an amusement and printed in the Lincoln (NE) Evening News on March 26, 1889. “Barrel of laughs” was printed in the Galena (KS) Republican on May 20, 1893.
 
In the second half of the 1900s, “barrel of laughs” began to be used sarcastically for a person who is not funny, as in, “He’s a real/regular barrel of laughs.” “Real barrel of laughs” was printed in The Palm Beach Post (West Palm Beach, FL) on August 8, 1966. “Regular barrel of laughs” was printed in the Tallahassee (FL) Democrat on February 2, 1967.
   
       
(Oxford English Dictionary)
In figurative phrase barrel of fun (laughs, etc.): (the source of) a great deal of enjoyment or entertainment. colloquial (originally U.S.).
1915   Dial. Notes 4 243   I had a barrel of fun when I went to Maccasin.
1939   L. Brown Beer Barrel Polka 4   Roll out the barrel We’ll have a barrel of fun.
 
Newspapers.com
19 May 1866, Manhattan (KS) Independent, pg. 3, col. 3 ad:
... I made the same successful hit on low prices this time that I made one year ago, when I made barrels of money and had barrels of fun in selling goods 50 per cent lower than they were sold two months before, ...
(Lewis Kurtz.—ed.)
     
Illinois Digital Newspaper Collections
8 October 1870, New York (NY) Clipper, pg. 209, col. 6:
OUD ON DER FLY—NO. 2.
WRITTEN FOR THE NEW YORK CLIPPER.
BY OOFTY GOOFT.
(...)
... dot vas a gay place, und many a barrel of fun your uncle Oofty had dere.
 
1 March 1871, Pomeroy’s Democrat (New York, NY), pg. 2, col. 5:
OOFTY GOOFISMS.
I’m been hafing a barrel of fun ladely—so’s Katrina.
 
Newspapers.com
19 August 1876, Ford County Blade (Paxton, IL), “Local,” pg. 1, col. 3:
Riley Swinford starts next Wednesday for the East and Centennial. Hope you’ll have a barrel of fun, Riley.
   
13 April 1877, Albany (OR) Register, “Election,” pg. 1, col. 7:
Should both Companies unite on the same candidate the election will not be unusually interesting; but should both Companies have candidates in the field then look out for barrels of fun.
 
Newspapers.com
26 March 1889, Lincoln (NE) Evening News, “Amusements,” pg. 4, col. 3:
It contains a whole barrel of laughs and they are judiciously distributed.
     
Google Books
March 1892, Table Talk, pg. 91, col. 1:
A BARREL OF FUN.
 
Newspapers.com
20 May 1893, Galena (KS) Republican, “The St. Felix Sisters,” pg. 1, col. 1:
This afternoon they play “Life in the Rockies,” a play with a barrel of laughs in every act.
 
Newspapers.com
6 January 1895, San Francisco (CA) Chronicle, pg. 20, col. 5 ad:
EXQUISITE SCENERY, a barrel of laughs, pretty girls, a great cast, sweet songs and the little Alabama coon at Stockwell’s.
 
OCLC WorldCat record
A barrel of fun; or, It’s good enough for the missions. A playlet for seventeen girl characters ...
Author: Alice Whitson Norton
Publisher: Franklin, O., Eldridge Entertainment House, ©1924.
Series: Eldridge popular plays.
Edition/Format:   Print book : English
 
OCLC WorldCat record
Barrel of laughs
Author: Edna Mitchell Preston
Publisher: New York : Scholastic Book Services, ©1959
Edition/Format:   Print book : Juvenile audience : English
       
Newspapers.com
8 August 1966, The Palm Beach Post (West Palm Beach, FL), “The Squirrel Cage: Caveman Party Was Her Idea” by Douglass Welch, pg. 10, col. 2:
Come to find out, she had seen something like this at Custer, South Dakota,where they built a cave man city for the entertainment of summer tourists with a bank, a theater, a city jail, a beauty parlor, and a whole bunch of other stuff like that, a real barrel of laughs.
 
Newspapers.com
2 February 1967, Tallahassee (FL) Democrat, “Soliloquy” comic strip by Hugo, pg. 4, col. 3:
OUR OLD I.R.S. OFFICE GANG USED TO SEE WHO COULD FIND THE BIGGEST LIE…THEY’D GAG IT UP ABOUT PENALTIES—A REGULAR BARREL OF LAUGHS…
 
Newspapers.com
22 September 1968, Poughkeepsie (NY) Journal, “No News Is Good News” by Gerry Raker, pg. 1-A, col. 1:
I said (after taking a tranquilizer) “Mom, you’re a regular barrel of laughs.”
 
Urban Dictionary
barrel of laughs
An unfunny or annoying person.
The term was originally used to refer to a funny person or situation, but is used sarcastically so often that the original meaning is all but lost.
Similar to laugh riot.
Yeah, he’s a regular barrel of laughs. Shoot me, please.
by Lady Chevalier May 11, 2005
     
Twitter
Yael Stone
@YaelStone
Oh these cabinet announcements are a real barrel of laughs *tries to laugh, starts to cry*
4:26 PM · Nov 18, 2016·Twitter for iPhone
 
Twitter
S
@Plasticdoe
Replying to @ReedRobertson@CaravellaBeth and 43 others
You’re being quite boorish. I bet you’re a regular barrel of laughs.
6:38 PM · Feb 21, 2018·Twitter for iPhone