.......Heartbreaker by Mariah Carey. Mariah Carey ain't what she used to be. I have been saying this for about 20 years. Whadayagonnado? But this day in 1999, Mariah was on top. Her 7th album, Rainbow, yielded her 14th #1 song, Heartbreaker, and also ushered in a new form of torture for music listeners; female pop songs with guest rap artists. MAKE IT STOP!! In this case, Carey collaborated with none other than Jay-Z and, like it or not, it was the very first commercial single by a solo artist with a guest rapper to hit #1 in the US and now there have been a trillion. WHY, MARIAH???? Heartbreaker also had a very expensive, Brett Ratner directed video that featured everyone's worst nightmare....two Mariah Careys! Again, WHY? I guess since the song went more R&B/hip hop she decided she needed to find the whitest person on earth to play her boyfriend. Enter Jerry O'Connell. Oh, and it's ripped off from inspired by Grease. Okay. Anyway, Heartbreaker hit #1 on October 9, 1999 and spent two weeks at the top. Here is the #1 song from this day in 1999, Heartbreaker.