The median household income in 1995 was about 56k
The median household income in 2018 was about 63k (we don't have numbers for 2020; this will be pretty close, I promise)
In 1995, $300 represented about 6.42% of the median household's monthly income
In 2018, $500 represented about 9.52% of the median household's monthly income
That's a pretty considerable difference. It's almost 50% higher in terms of how big a strain it puts on a given household's income
And that's not even half the picture!
Given that living expenses keep pace with inflation (or even higher) rather than income, $500 is even more expensive! In the context of an economy where everything's more expensive and people have less to spend in general, more of that median income goes toward keeping people alive. The amount of money we can spend on entertainment is lower, but everything costs more!
$500 now is a lot more expensive than $300 was in 1995, for a variety of reasons. Hell, $300 now is more expensive than $300 in 1995, for a lot of people!