A few years back, I did a little exercise, to see how my portfolio would have held up if I had retired on 12/31/07, and had to start relying on it, using my actual portfolio returns over the years. While 2008 was a bad year, the recovery was so fast, and everything since then was smooth sailing, so I quit updating it at the end of 2017. And, while 2018 ended up down a bit, 2019 was a great year, and despite the COVID fiasco, 2020 was good as well. So chances are, I'd still be fine even now. I ran scenarios with a 3%, 4%, 4.5%, and even a 5% withdrawal rate. Even at 5%, if I had started with $1M on 12/31/99, I would have ended up with around $994K on 12/31/17.
I also ran "what if" numbers, presuming I retired on 12/31/99. That scenario is definitely shakier, and I carried this one out through 12/31/20. At 3%, that $1M would be at around $917K. But at 4%, I'd be down to around $150K, and definitely on track for failure within the next couple years.
Now, there are a few flaws in my calculation, though. First, if I had been close to retiring, I probably wouldn't have had my portfolio invested nearly as risky. Also, at some point, SS would have been kicking in.
I have a feeling that retiring in 1999 is probably one of the roughest cycles in recent memory, but even it wouldn't have been a total disaster, if you had planned wisely.