The least creepy IMO is when you would see a television or radio host cut away to promote a product which directly tied the content creator to the promotion.
Later that became less common and advertisers approached content aggregators like Television networks who maintained a carefully curated collection of content this wasn't too bad.
The current trend of advertising companies selling ads on non-curated, user generated content seems to have crossed a line where major problems are just inherent. I think a better arrangement would be if Google and Facebook allowed content creators and advertisers to directly connect thereby allowing each to choose what sort of brands match their particular image.