Bidding on legal terms

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Just bid on Oprah. It's fine.

lmao - that was my exact introduction to affiliate marketing in 2004. There was an email submit for a free "O" magazine on one of the bigger networks. I threw up an adwords campaign bidding on Oprah direct linking to the offer and ended up making $400/day for a while.

End of my story, but to answer the OP, you can typically get away with it unless they're extremely mainstream. I believe you'll be able to bid on just about any name after the trademark protection is lifted in June but you'll probably have to answer to their attorneys if they feel it's necessary to protect it.
 
As long as the advertiser is ok with it (and they will explicitly say when they aren't), the worst that can happen is that you'll be asked to shut down your campaign.
 
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