Song: "Rapper's Delight" by The Sugarhill Gang
Level Of Embarrassment: Kind of awesome, actually

Oh, your grandma's cool? Sorry if we steal the "Coolest Grandma" mug from her cabinet and give it to someone more deserving: Ellen Albertini Dow. She's the only one who has earned that mug, buddy. She looks like she's four-foot-nothing and just a step away from a shattered hip, but that doesn't mean she doesn't know hip-hop, know what we're sayin'?

She only sings a little of the longest song in history, "Rapper's Delight," in a wedding reception scene in The Wedding Singer, but anytime we hear that song, we still picture that little granny's joy in performing it for a crowd. Pretty adorable stuff. TA