Drake
Drake bit off considerably more than he could chew when he invited Madonna on stage at Coachella in 2015. The Material Girl wet-kissed his face off, leaving the Canadian visibly repulsed as he wiped his mouth afterwards.
Still, to be fair Madge may have been the most embarrassing one of the two here – a crown that the rapper nevertheless neatly wrested from her by exhibiting his terrible dad dancing in the video to “Hotline Bling” five months later.