Great question! I don't know the answer, but it would be interesting to figure out. However, the version of the catalog probably changed over time.

This Acaeum thread has a lot of random catalog/advertisement info:
viewtopic.php?t=4298&start=0
This Tome of Treasures page is more orderly, with one thread per catalog:
http://www.tomeoftreasures.com/forum/vi ... php?f=2085

There are two versions of the Gateway to Adventure catalog. This is the earlier version, which is the oldest "full color" catalog posted in either of the above links:


Here it's speculatively dated (based on its contents) to 1979 or 1980:
http://www.tomeoftreasures.com/forum/vi ... php?t=4120

There's also a contemporaneous version with the same artwork, but in black and white monochrome:

Seller's description: "We are also including "Gateways to Adventure" which are 1980 retail order forms and 6 page color catologue."
Included in auction with a 4th+ Print [Holmes] Basic Set
It looks fairly thick, so there must be a large number of the order forms if the catalog is only 6 pages long.

I never heard a clear description of what was contained in this version. By the seller's description of "retail order forms", it sounds similar to the "Retail Order Blanks" - basically the catalog of the The Dungeon! shop, which later became the TSR Mail Order Hobby Shop.

Here's a 1981 version of The Dungeon "Retail Order Blanks":


I'm pretty sure there are earlier versions of this. In the last post in the Acaeum thread, I posted this oddity that was auctioned on Ebay:



It looks like a retailer-customized version of the Order Blanks. They have a date of 5/79.

I wouldn't be surprised if there are even earlier catalogs that haven't been posted to either of the above threads.

The Gateway to Adventure catalogs are common since they seem to have been shipped with Holmes and Moldvay boxed sets. The order forms are rarer, since (I think) they were only obtainable by ordering them from The Dungeon!. They may have sent one out with each order. When I ordered from TSR in the late 80s they would always include a new catalog with each order.

I was looking back at the old catalog thread (first one I linked above) and noticed in the first post I mentioned that the ad shown there refers to a color catalog. This ad has a Lizard Logo, which dates it to pre-1978. Then I was looking at the ToT Dungeon Hobby Shop thread that Mars linked above (which I missed the first time around - thank you, Mars), and found this early color catalog titled "Games for Imaginative People", also with a Lizard Logo:

http://www.tomeoftreasures.com/forum/vi ... php?t=4274

This catalog looks like a predecessor to the Gateway to Adventure catalog, and is a possible candidate for both the color catalog mentioned in the ad, and the $2 catalog mentioned on the back of early modules and rulebooks (e.g. Holmes Basic 2nd print Lizard Logo mentions the $2 catalog). On the other hand, this color catalog also refers to the $2 catalog (see pg 3, section "Dice and Accessories"), and makes it sound more extensive (including things like belt buckles), which it makes it sound more like the Retail Order Blanks. The 1978 Blanks that Mars linked above include accessories like the TSR belt buckles (pg 5, "Accessories").

I wonder at what date TSR stopped charging for the catalog?

Edit: Holmes 2nd print mentions the $2 catalog; the 1st print does not. Potentially dates first appearance of the $2 catalog to between 1977 and Jan 1978.

I have seen 2 (I believe) other TSR colour catalogs for TSR stuff in the same format as that one.