Wikipedia even specifically says that Oldman was hard up for work between 2001 and 2004.
Guardian writer Xan Brooks described the early 2000s as Oldman’s “low point”, recalling “barrel-scraping roles” in the 2003 films Tiptoes and Sin .
I was thinking David Warner - twice-divorced in the right timeframe with two kids and a fair number of sci-fi and/or villain roles, but he doesn’t seem to have had any issues getting work at any point in his career. Not sure if either of his wives were actresses either.
On the other hand, his film and TV work immediately post-9/11 doesn’t appear to be much to talk about.
It occurs to me that short of someone producing a program for a Las Vegas convention held at that timeframe I’d have no way of knowing for sure but Oldman seems the best bet. I’m certainly willing to accept that as an answer to something that has been niggling at me for a few months now.
“A fair number”? David Warner is the best villain in movie history, and I can prove it.
He is kind of awesome at it. On the other hand, it made it a pleasant surprise when he turned up as a good guy in things.
How long does child support last? Malcolm McDowell was married to Mary Steenburgen, and they had two children, born in 1981 and 1983.
What things?
His Babylon 5 appearance comes immediately to mind. He came looking for the Holy Grail.
Turned out they had already got one. It was verra nice.
Generally 18 years, but if you didn’t pay the arrears remain collectable.
I had actually thought about suggesting Malcolm McDowell myself. It’s possible his child support arrangement lasted through college for his kids, which would put it in the right time frame. He’s about as WASP-y as you can get without a stinger, and he played a number of villains in sci-fi and sci-fi adjacent productions.
Against that, he seems a bit high profile for the anecdote, and looking at his filmography, I don’t see much of a fall-off post 9/11.
The description of “a serial SF villain”, having difficulty making child support payments, and being at least implicitly paired with Jerry Doyle, really makes it sound like someone who worked primarily in TV and direct-to-video productions, not someone with Malcolm McDowell’s profile. So, I think doubtful, but maybe.
I’d missed reading that part in your OP; it would seem to make the odds of the convention being able to draw bigger stars more likely than if it’d been in, say, Minneapolis or Columbus. 
I never watched it. I honestly can’t remember if I’ve ever seen David Warner play a good guy. He was evil personified in Time Bandits.
With interest, and sometimes it can be a heck of a lot of money. In some states, punitive fines can be added. If McDowell’s support was high in the first place, then it’s possible that because he missed a few payments for whatever reason, it really could have built up, and he could have had some difficulty coming to an agreement on how to pay it in full.
This, too. And this can lead to squabbles, if there was a blanket promise to pay “for college,” then the kid gets accepted to a very expensive school.
Lorraine Bracco and Harvey Keitel did actually live together, and I think a lot of people thought they were married; on the other hand, I don’t think the fight over their daughter’s custody was about money; it was about time.
Probably an obscure actor who appeared in one of these but i cant find more like an official listing of guests
You guys have mentioned all the obscure likely ones, in addition none of
Terrence Stamp
William Smith
Anthony Michael Hall
Anthony Zerbe
Fit the bill.
After I read the OP, I searched for a few minutes, and came up with Gary Oldman, who others have mentioned.
According to the quote, the painful divorce is not necessarily the mothers of his children. “Uma opened up about how “hard” the divorce was in an emotional TV interview with Oprah Winfrey in 2005.” Though they were divorced in 1992, so that’s a long time to be talking about a painful divorce.
I just re-watched Willow, which suggested a possibility, although a dubious one: Gavan O’Herlihy.
He ticks several boxes. I’m not sure I’d describe him as “a serial SF villain”, but he did mainly play villains, was in several SF or SF adjacent projects, is pretty darn WASP-y, and after working steadily from the mid-70s to 2002, his career fell off a cliff (51 film credits from 1973-2002, more than one a year on average, then nothing in 2003, 2004, or 2005, one credit in 2006, nothing in 2007 or 2008, two in 2009, and nothing more until 2021 with one project currently in production).
There are a couple of problems. One is that I haven’t been able to find any information on his private life. That doesn’t rule out a marriage and subsequent painful divorce, but if he had been married to an actress, and if he were in the habit of complaining about his divorce to random convention attendees, one would think his marriage and divorce might turn up in his online bios. The other issue is that he apparently permanent relocated to the UK in the 90s, so it seems a bit unlikely he’d show up an SF convention in Las Vegas in the 2000s.
But maybe?