In hindsight, it's really hard to overstate how quickly America did a heel-turn over gay issues in such a relatively short time period. I definitely remember friends using gay and fag well into the late 00's, even 10's. And looking at the political scene, gay marriage is one issue that really came into acceptance in an unprecedented way. Paul Wellstone, probably the most left-wing senator at the time, voted for the Defense of Marriage Act in addition to most other Democrats. Hillary and Obama were both opposed in the '08 election. Now it's basically heresy if you don't support it, and very few Republicans will go up to bat in overturning it.Gay jokes were still very much a thing in pop culture, and teenagers often used gay as an insult all throughout the 90's and 2000's, but true and honest full-on homophobia and gay bashing was condemned, especially after Matthew Shepard got killed.
"Casual homophobia" of jokes and ribbing was acceptable, but was also kind of seen as childish and immature as you got older, especially as the 90's gave way to the 2000's. Like, it was okay and expected if you were a kid or a teen, or even in your early 20's in some areas.
But once you hit your late 20's/early 30's, being openly homophobic was seen as pathetic unless you were an outright redneck or hood rat. Everyone had a more "none of my business/you do you" mentality for most of the 90's and 2000's, barring the fundies or fringe groups like the lefty proto-SJW's and OG Antifa punks or Neo-Nazis and Militia spergs.
Actual homophobia involving physical violence or threats was a huge no-no even back then.
Looking back, even in the past 10 years the overton window on what is socially acceptable has shifted greatly. Watch some old Louis CK bits or early episodes of It's Always Sunny and you'll be bombarded with jokes that they wouldn't be caught dead making now. And if you told people just 10 years ago that virtually every media outlet and corporation would cheer on people burning down their own cities and disbanding the police in the name of justice, you would be considered insane.