Ahh, Valentines’ Day. If you were born before 1984 (est.), you probably were still engaging in a bit of lovelorn mix tape exchanges with various objects of affection.
Idolator has listed seven all-time creepy songs that likely appeared on some of these mix tapes, accompanied by music videos. Winger, Ringo Starr, Rod Stewart and Extreme all make an appearance.
Admittedly these were before my time, and my mixes were more along the lines of ballads by the Magnetic Fields, Morrissey, and Sebadoh, but these videos are a lot more entertaining than any of those would likely be.