Yep, I did this once with "Credit card services" and after about 20 minutes, I had gotten all the way to level 3. Level 2 was a hapless individual, but level 3 was a smooth talking ahole that was amazingly adept at manipulation. When I hung up he immediately called back and I told him I had been called dozens of times by this scam and this was my way of getting back at him. Click. 20 seconds later my phone rings and a person is screaming at me, telling me he wants off the list, etc, etc.

I unhooked my phone and called AT&T and tried to report it. They tried to get me to go through some absurd process and I dropped it.