Taylor Swift Video: Live in the Billboard Cafe (2006)

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4. TAYLOR SWIFT "Speak Now" Taylor Swift Up Close

Back when a 16-year-old Taylor Swift first released her self-titled debut, Billboard knew she was something special. The album went on to sell millions and reach No. 5 on the Billboard 200 Chart, and a star was born.

In Billboard's first video with Taylor, from 2006, she performs her breakthrough hit, "Tim McGraw," live in our New York headquarters. Swift's not shy about her life story in the clip's interview, despite her young age.

She warns in the clip: "If you break my heart, hurt my feelings, make me feel really bad, or are really mean to me, I'm gonna write a song about you." In light of "Speak Now," perhaps Kanye West and her ex-boyfriends should have paid attention.

Video: Taylor Swift Performs "Tim McGraw"

In our next video with Taylor, also from 2006, she performs "Mary's Song (Oh My My My)" at Billboard's offices and gives us the inside scoop on what inspired the song.

Video: Taylor Swift Performs "Mary's Song (Oh My My My)"

When Taylor re-released "Fearless" in October 2009, Billboard was there to catch up with her about the additional songs and video extras that were added to her second album.

Video: Taylor Swift Talks "Fearless" Re-release