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Better do it during taxi missions.
Took over an hour to get to the ads on each radio station talk shows included.
Also had to switch to a different station at the end of it for it to pop.
#Pain
If you accidentally leave your car then you'll have to repeat it from the beginning.
There's also a talkshow radio which takes 15-20 minutes for one full cycle so you have to be patient.
I finished it while doing the 100 taxi rides just at the beginning of the game and it was one of the first achievements that popped up for me.