This article is a couple of weeks old, but I had to make note of it here because it's the most interesting idea for a list I've seen in forever. Considering that 95% of entertainment-related media is made up of lists, it's rare to see a list that to my knowledge has never been done before, even in a vaguely related form.
Honourable mention could have gone to Gordon Lightfoot for re-recording half of his greatest hits for "Gord's Gold". The re-recorded versions are now by far the most well-known versions, although technically they don't qualify for the list because they weren't new songs. Unless you count "I'm Not Sayin'/Ribbon of Darkness" and "For Lovin' Me/Did She Mention My Name" as new songs in their joined forms.
I can't remember why Tupac sampling Bruce Hornsby and the Range wasn't a bigger deal ... or maybe it was? Thugs belting out the chorus to an 80's MOR hit? Did Puffy completely steal his thunder the year before with "I'll Be Missing You"?
It makes sense that Lenny Kravitz and Madonna would show up here because, as noted in the text, their music is best represented by their singles, even though they worked in album-dominated eras. It's especially surprising in the case of Kravitz, who released his best known material in the 90's when the CD album was just about the only music format available.
The list loses me at #2 and #3. Neither song really ranks among the best of Tom Petty or Depeche Mode. Janet's "Runaway" is a reasonable choice for #1, but I don't think it stands out from her other singles in the same way that "Lady" does for Kenny Rogers, or "Again" does for Lenny Kravitz. I would have ranked those two at the top in some order, although you could make a good case for "Raise Your Glass" too. #4 would have to be "Justify My Love" -- it's not Madonna's standout song (although up until the "Evita" era it basically defined her 90's sound and image) but it's a personal favourite.