I feel like billboard ads for actual brands were on billboards in racing games in the PS2 era. Or like product placement for a Nokia Sidekick or something.
One of the most asinine things I’ve seen was some ultra graphic “realism” mod for GTA V and they replaced all the fictional, creative advertisements and brands for real life billboard ads from McDonald’s, coke, marvel, etc.
They had a live update system for Burnout Paradise and whatever the latest Battlefield was back then which allowed them to change the ads displayed on in-game billboards, some of which were Obama's campaign ads.
EA has really been at the "forefront" here though, I remember when they put a Rexona ad in the pause menu of one of the late 90s FIFA games.
Real brand ads are going to be a thing in any racing game that has a real world license. Or even without a license, since Pole Position had Marlboro and Pepsi billboards in 1982.
One of the Need For Speed games definitely had serious product placement for the Sidekick (which was not a Nokia phone btw).
I know in Battlefield 2142 they had generated ads on billboards. The game came with a little card in it telling you that by playing the game you agree to the terms of the ads.