How historically accurate is the film "Office Space"?

I wouldn't look at the main occupation of the characters in the movie as some attempt at being historically accurate to the times.

As noted on Wikipedia:

Shot primarily in Austin, Texas, the origins for Office Space lie in a series of four animated short films about an office drone named Milton that Mike Judge created, which first aired on Liquid Television and Night After Night with Allan Havey, and later aired on Saturday Night Live. The inspiration came from a temp job he once had that involved alphabetizing purchase orders and a job he had as an engineer for three months in the Bay Area during the 1980s, "just in the heart of Silicon Valley and in the middle of that overachiever yuppie thing, it was just awful". The setting of the film reflected a prevailing trend that Judge observed in the United States. "It seems like every city now has these identical office parks with identical adjoining chain restaurants", he said in an interview. He remembers, "There were a lot of people who wanted me to set this movie in Wall Street, or like the movie Brazil, but I wanted it very unglamorous, the kind of bleak work situation like I was in.

Possible reasons Judge chose software developers:

1. As noted in the excerpt from Wikipedia, he worked briefly as an engineer working in what became Silicon Valley, so Judge is mostly drawing from his own, personal experiences and not necessarily from the industry as a whole.

2. Tech companies were on the rise in the late 90s.

The occupation of the main characters wasn't chosen to necessarily be an accurate depiction of that specific job at that point in time, but (possibly) more so due to their increasing visibility in the economy at the time (remember, the dot com bubble would burst within a year after the movie's release). Given his experience as an engineer, the impending Y2K "bug", and people's misconceptions about computer systems in general, he could also write the characters as being successful in "getting back" at their employers who clearly didn't care about them by developing a simple piece of code that could rip the company off.

In the end, the movie is really meant to be taken as more of a satire than anything else, providing people with a laugh that they can relate to.

There were certainly many similarities to corporate work in general, especially during the dot com bubble era.

Some negatives:

1. The presence of multiple, irritating program managers that are passive aggressive
2. A requirement to fill out useless paperwork just because it is corporate policy (TPS reports?)
3. Being stuck in traffic to and from work
4. People being fired from their jobs for no reason other than an arbitrary corporate goal to fire some people
5. In the US at least, people being cheerful at all times.

These and other things were 100% nailed by this movie, combined with a lack of real motivation for some workers.

On a positive note, his relationships with his friends and his neighbor are also present in the workplace.

I think that being a well-paid techie in the 1990's was good, just as now. But as with the corporate world, there is always a level of dystopia to it.