Rob Thomas is famous for many things: fronting American rock outfit Matchbox 20, guest starring with an almost wordless performance in an episode of 'It’s Always Sunny in Philadelphia,' being a ‘90s heartthrob. But he is known mostly today for the Grammy Award-winning song “Smooth” by Carlos Santana featuring Rob Thomas of Matchbox 20. The gargantuan smash hit single from Santana’s 1999 LP 'Supernatural' has taken on a life of its own in recent years, becoming one of the internet’s sweetest memes, a gift that keeps on giving.br br Watch him take on the "Smooth" themed 'Would You Rather' above.