TV show and album: Who's The Boss? and Do You See Me?
Though she was just a kid when Who's The Boss? premiered back in 1984, Alyssa Milano, the television daughter of Tony Danza, was a smoking hot 20-year-old by the time the series wrapped up in 1992. And in case you forgot (or didn't even know) she sang, Milano also released her fourth studio album, which only ever charted in Japan, that year.