While this doesn't push the date back any, it provides some insight into what happened in August/September 1999. You definitely still had access to your student account, and you made a post on Usenet about what had happened:

http://groups.google.com/group/rec.arts.comics.str ips/browse_thread/thread/31f7d1ee3f52f0db/77021a82 e47053ec?hl=en&q=#77021a82e47053ec [google.com]

Unfortunately none of your other posts say anything about when you started Sheldon.

It seems we've already gone backwards past this date, but Comixpedia states with seeming authority that the strip started on June 21, 1999.

I wonder what their source is, and whether knowing what source they're looking to might provide another avenue of investigation.

Following @Maestro's lead, usenet gets us back to August 8, 1999 http://groups.google.com/group/rec.arts.comics.str ips/browse_thread/thread/95c639b3995a94c1/48e23bc1 3edc2341?hl=en&q=&fwc=1, but it only references the "new" www.davekellett.com website that you would be transitioning to on October 1, 1999.
The key to finding older dates (failing your having fans in Kent's IT department) will likely be from secondary sources that may include you discussing a "new" update.

No offense Dave, but I don't think you went back and updated your pages much, if at all. I say this because on August 31, 1999 you DID update sheld63.html. That was when you apparently decided to start naming your comics by date. I'm guessing that you only updated your comic pages when a new comic came out. Since the 'next comic' link was to 990831, and that's the same as your 'last updated', I'm guessing you weren't in the habit of going back through and making updates much.

Anyway, working back through the archives tells us that June 8 is a very good possibility for a second comic to have come out. If you updated comic 1 to add in the 'next comic' link on the same date you posted, and then made no further updates to that page before Internet Archive took its snapshot in december, then while we can't say for sure when comic 1 went up, we can at least say it was probably a day or two earlier.

June 7 1999 was a Monday, and I'm guessing you probably started your comic with the intent of keeping a M-F schedule. So, that's what I think your definitive start date was.

Follow this link to see all the pages Internet Archive has for your old personal site: all djk3 [archive.org]

Notice that it skips everything between sheld1 and sheld35, but when it picks up again, it has sheld35 out through sheld63. Those comics show a steady progression in their 'last updateds' that makes June 1999 a very likely starting month.

Dave, I just went through the math to be sure, and if Monday June 7 was really day 1, and Monday July 19 was day 37 (aka the day 36 [archive.org] got updated with the 'Next comic' link), then posting a Mon-Sat schedule gets you back to June 7 as day 1, without missing even one single day.

In Response to sheepster (#47129):

@sheepster: The use of the footer is because Dave was following the rules outlined on the rules page [archive.org]

specifically this one:

"You should sign and date all your pages to allow readers to know how to contact you and how relevant the information given may be."

Thus, the dates are not server-added, they're Dave-added (further supported by the fact that the rules page itself uses a different format than Dave's page, even though they are on the same server).

It could be possible that he missed updating one or two dates at some point. However, most likely they are automatically generated by the editing program that was used, so that does give them some validity.

... if we assume Dave didn't bypass his usual editing program in favor for a quick change in notepad or something.

Aha. A well-researched point. I'll have to concede that one. Though two pages say that it was May 19th at different times of the day. Then again, maybe Dave was having a forgetful day.

That web-page does make me laugh though:

"WARNING: Remember that potentially anyone in the world could read your pages; including future employers or members of your family, so only publish information that you don't mind anybody in the world reading!"

I like the fact that people had to be told this at one point. It reminds me that we were once an innocent people.

It's worth noting that since we know Dave used MS Word, the timestamp was almost certainly generated with a tag in the footer. Every time he used Word as his editor, the timestamp tag updated automatically according to when he saved his document as HTML. If he used notepad, the tag wouldn't have updated. If he waited a day between when he saved his page and when he actually uploaded it to his site, the timestamp would still show the previous date.

That said, it seems to me that he changed all his pages when he started posting Sheldon. He probably created those footer links in one document and then did a copy-paste into the others, as well as updated his template for any future pages. Sure he could've used notepad there too, but being a structural change rather than a minor edit, I'd guess he probably used Word. I'm starting to come around to May 19 as the most likely start date. It just means he missed a lot of days there at first.

But Dave, is it possible you started putting together the first few weeks' worth of strips in advance, and then began putting them up after you had a cushion of work? That would explain how your strip 'Sheld35' is dated July 31 on the calendar links, but July 19 on its own 'last updated'. That date was when you last saved the Word doc, and not necessarily when it got uploaded. If that calendar really was correct about the dates the comics came online, then suddenly the June 21 date starts to seem possible.

In Response to sheepster (#47166):

I like the fact that people had to be told this at one point. It reminds me that we were once an innocent people.
Don't be silly--people TODAY still need to be told that, too.

I realize Dave has already heard this in an email I sent him, but I wanted to get this theory out among the other readers.

Archive.org saved two snapshots of Dave's homepage index. The first snapshot it took on August 31, 1999. In it, every date on the calendar is filled, save one on August 30. Archive.org's second snapshot was taken a few months later, and on that one, there is a fairly large gap in the September calendar, with only a single comic posted between September 9 and 20.

Both of these pages are telling. The second one tells us that he moved his comics to davekellett.com sometime around the end of September or the beginning of October. Related, I happened to find an article [suite101.com] linking to davekellett.com as a new comic, dated 9/21/1999, so the gap might have been when he was working on putting together the new site.

The first page tells us that, at least initially, he tried to keep a daily schedule. More useful though, we can put possible published dates with each of the comics labeled 'sheld35' to 'sheld63'.

When you go to these actual pages, you see dates that range from July 19 to August 31. But they tend to be clustered, such that several comics could be all updated the same day, and then be followed by a long gap. And when I try to imagine what would cause that, I envision Dave making these comics on his computer - saving them with a Word timestamp, and then later uploading them on the appropriate date.

And the fact that as the comics progress, they get closer and closer to the date on the calendar, that makes me think he probably tried to keep a cushion of work ahead of him, but it dwindled away as he had trouble keeping up.

Now, Dave probably did first get the idea of giving Sheldon his own online comic back in Fall of 1998, and might have even played around with his college's personal homepage setup to see what a comic would look like online, but I don't think he embarked on his ambitious goal of daily updates until he had a few strips already done. Maybe they were the 30 or so he drew in order to send to various syndicates.

But anyway, once he started, it seems he put a new comic up every single day, until August 30, when he finally didn't get one done in time and had run out of reserves. But working backwards, it would put "Sheld 1" as (not necessarily the first time he placed it online, but first time he promoted it) going up Monday, June 28, 1999.

I could be totally wrong, but since we'll probably never know for sure anyway, I saw no reason not to throw a last suggestion into the mix.