Remember When Kellie Pickler + Taylor Swift Teamed Up?


We all know they’re friends, but do you remember when Kellie Pickler and Taylor Swift teamed up for a Top 10 hit?

Pickler came to national attention when she hit the stage of American Idol during its fifth season, placing sixth. She released her debut album, Small Town Girl, later that year, within a week of the then-unknown Swift releasing her self-titled debut.

How Did Kellie Pickler + Taylor Swift Meet?

Both albums were successful, and the young ladies hit the road for a tour with Brad Paisley that saw them become fast friends.

What Song Did Taylor Swift and Kellie Pickler Collaborate On?

They collaborated on a song called “Best Years of Your Life” that was inspired by Pickler’s own love life.

“I had went through a really bad breakup a while back, so we wrote the song about the relationship that went sour,” Pickler recalls to the Boot.

Swift joined Pickler in the studio to provide background vocals for the track, and she also appeared in the video for “Best Days of Your Life.”

How Did Kellie Pickler’s “Best Days of Your Life” Do in the Charts?

Released as the second single from Pickler’s self-titled sophomore album on Nov. 5, 2008, “Best Days of Your Life” reached No. 9 on Billboard‘s U.S. Hot Country Songs chart, giving the singer her biggest chart hit to date. It was certified Gold on July 2, 2009.

“It’s so funny, because Taylor always says that she has the “Picture [to Burn]” song, and Carrie Underwood has “Before He Cheats” … and now “Best Days of Your Life” — that’s my kiss-off song!” Pickler says. “[My ex] has heard it, and so has the person he’s with now, so I guess it’s bittersweet.”

PICTURES: Kellie Pickler Returns to the Stage at the Ryman Auditorium

Kellie Pickler returned to the stage for the first time since her husband Kyle Jacobs’ death at the Ryman Auditorium in Nashville on Monday night (April 22), performing as part of a tribute to Patsy Cline.

Gallery Credit: Sterling Whitaker





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Graham Haring

Graham Haring is a versatile writer with a knack for capturing the heart of country music and the stories that surround it. Covering everything from new song releases by icons like Tim McGraw to unexpected cultural phenomena like "The Waffle House Index," his articles bring a mix of humor, depth, and curiosity to the table. Graham’s work often explores the personal side of country music, highlighting the community, family moments, and heartwarming stories behind the headlines. Whether it’s about Keith Urban's benefit shows or a quirky note from the past, Graham's writing resonates with country fans who appreciate a touch of authenticity and a good story.

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