"When should you go on a cheese…

“Cheddar” sounds a bit like “shed a.” “He went on a cheese diet in order to cheddar few pounds. (Pun of the Day)” was posted on the newsgroup alt.callahans on July 27, 2001. The joke originated on the Pun of the Day website.

A cheese riddle version was posted on Twitter by Dave Niker on July 17, 2012:

Q: When should you go on a cheese diet?
A: When you need to cheddar a few pounds.

Wikipedia: Cheddar cheese
Cheddar cheese is a relatively hard, off-white (or orange if colourings such as annatto are added), sometimes sharp-tasting, natural cheese. Originating in the English village of Cheddar in Somerset, cheeses of this style are now produced beyond the region and in several countries around the world.

Google Groups: alt.callahans
Puns of the Weak 7/27/01
Stan Kegel
Jul 27, 2001, 11:27:05 PM
(...)
He went on a cheese diet in order to cheddar few pounds. (Pun of the Day)

Google Groups: alt.humor
Puns of the Weak 03/15/02
Stan Kegel
Mar 16, 2002, 1:15:11 AM
(...)
A guy went on a cheese diet in order to cheddar few pounds (Pun of the Day)

Google Groups: alt.humor.puns
Puns of the Weak 12/06/02
Stan Kegel
Dec 6, 2002, 11:47:10 PM
(...)
I went on a cheese diet to try and cheddar few pounds. (Pun of the Day)

Twitter
Cheese Jokes
@dailycheesejoke
He went on a cheese diet in order to cheddar few pounds
11:05 AM · Oct 6, 2009·Twitter Web Client

Twitter
Kayleigh_Pincurls
@Kpincurls
Replying to @qikipedia
@qikipedia why did the woman go on a cheese diet… in order to cheddar few pounds #crackerjoke
6:55 PM · Dec 22, 2011·Twitter Web Client

Twitter
Joe Earley
@joeearley
Why is the cheese diet so popular?
It’s a great way to cheddar few pounds
#CheeseJokeFriday
7:42 AM · Mar 9, 2012·Twitter Web Client

Twitter
Dave Niker
@daveniker16
@ljh123 @jennyctweets @DanJRobbo18
When should you go on a cheese diet?
When you need to cheddar few pounds
#cheeseytuesdays
4:55 PM · Jul 17, 2012·Twitter for iPhone

Twitter
The Cheese Festival
@TheCheeseFest
Cheese joke of the day!!!
Q: When should you go on a cheese diet?
A: If you need to cheddar few pounds!
8:22 AM · Aug 22, 2012·Twitter for iPhone

Twitter
Puns of The Day
@RandomPun
He went on a cheese diet in order to cheddar few pounds.
3:00 AM · Jan 9, 2014·RandomPun

Twitter
sickipediabot
@sickipediabot
I’m going to try the new cheese diet.
Hopefully I’ll cheddar few pounds.
1:33 PM · Feb 3, 2014·sickipediabot

Facebook
NaturKur Wellness
May 29, 2017 ·
Q: When should you go on a cheese diet?
A: If you need to cheddar a few pounds

Twitter
Shit Jokes
@ShitJokes
When should you go on a cheese diet?
When you need to cheddar a few pounds.
11:36 AM · Sep 12, 2017·Twitter Web Client

Twitter
Shit Jokes
@ShitJokes
When should you go on a cheese diet?
When you need to cheddar a few pounds.
1:56 PM · Jan 20, 2018·Twitter for Android

Twitter
Boro Campus Rec
@borocampusrec
When should you go on a cheese diet?
When you need to Cheddar a few pounds.
Don’t forget it’s arm day today! Time to work on them muscles, you are doing a great job and keep up the hard work!!
6:00 AM · Sep 8, 2020·Hootsuite Inc.

“When should you go on a cheese diet?”/“When you need to cheddar a few pounds.”