Back in 1989, Gloria Estefan was pretty much on top of the world. She had a new lead single, “Get on Your Feet,” which would become the name of her forthcoming world tour (that tour was cut short by a near-fatal bus crash). The song rose to number 11 on the Billboard Hot 100.
Since then, the song has been used sparingly, but extremely effectively, in pop culture. My vote for most awkward use has to come from Steve Ballmer, CEO of Microsoft, who went nuts to the song during his introduction at an internal employee-only pep rally back in 2001. This is the type of dance I do in my room when no one is watching.
So that would be the pick for most awkward, but then Parks & Recreation used the song in this amazing bit. This is so awkward, but hilarious.