Why do so many country singers make songs complaining about being poor?

Because the songwriters aren't often the singers. Also, most don't get paid for gigs in Nashville. They do it for tips, and the hope of being discovered.
 
A lot of the original country artists were down on their luck, depressed guys who had very hard lives. They wrote songs that the everyman found relatable, and modern day country singers are still co-opting the suffering of those who paved the way for them. Like how every rapper was a gangsta/killa for a while because some of the original rappers were legitimate murderers who were involved with gangs.

Country makes me want to rip my hair out because they sing about the same five damn topics in EVERY song, I swear. There's almost no experimentation lyrically or musically, and that's what the low-IQ fans enjoy, even when their songs sound indistinguishable from hip-hop because they're so processed.
 
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I love money, solid workhorse vehicles, and a lady's curves. I'm a healthy red-blooded American man. It's also part of the culture, America is a nation of temporarily embarrassed millionaires.
(Hold on, my wife has informed me that there's only one woman's curves I can appreciate, oh well.)
Bo Burnham made a song pretty much shitposting at the second wave of these guys.
 
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