Fourteen years ago, on April 23, 2009, Taylor Swift launched her first headlining tour with a sold-out show at the Roberts Municipal Stadium in Evansville, Ind. The trek -- which was dubbed the Fearless Tour -- was, appropriately, in support of the star's sophomore effort, Fearless, which topped the U.S. country and pop charts upon its release in November of 2008.

Swift's Fearless Tour wound through the U.S., Canada and England through November of 2009, then picked back up in Australia in February of 2010, before concluding with another North American leg from March to May of 2010. She also opened several shows for Keith Urban (and one for Kenny Chesney) and performed at select festivals during the run.

Prior to launching her Fearless Tour, Swift warmed up by playing two shows in Texas (including a sold-out gig at the Houston Livestock Show and Rodeo) and one in Florida. However, it's clear that kicking off the extensive tour meant a great deal to her.

"Headlining my own tour is a dream come true!" Swift said in a press release announcing the tour. "This way I can play more music every night than I ever have before. Having written my own songs, they are all stories in my head, and my goal for this tour is to bring those stories to life. My favorite thing when I go to a concert is having lots of changing things to look at, so I've been working really hard to make this show as multi-dimensional as possible."

As a result, the release went on to note, Swift would be playing "five different guitars, as well as the piano" and make "multiple costume changes" each night; the latter included including a marching band / majorette outfit (replete with a massive hat) and multiple sparkly dresses. If that wasn't impressive enough, Swift's Fearless Tour shows also featured "an incredibly theatrical presentation of graphics, sets and visual elements designed by Taylor herself" and "a fairy-tale castle illuminated by more than a million lumens of light."

Swift's Fearless Tour setlist, appropriately, drew heavily from Fearless and her 2006 self-titled effort, with hits such as "Tim McGraw," "Teardrops on My Guitar," "Fifteen" and "Love Story" appearing regularly. Swift also meticulously arranged the set to have three distinct sections, including an acoustic segment, which became a staple of future concert tours.

Opening acts on the 2009 North American leg of Swift's Fearless Tour included Gloriana and Kellie Pickler. (Believe it or not, then-burgeoning pop star Justin Bieber opened some dates in the UK.) As she would come to do on many future tours, Swift brought her openers onstage during her own set; below, watch Gloriana and Pickler collaborate on a performance of "I'm Only Me When I'm With You."

As the Fearless Tour soldiered on, Swift's popularity continued to grow. Fearless was certified quadruple platinum on Sept. 10, 2009, on the strength of the crossover success of "You Belong With Me" and "Love Story." The tour's ticket prices also helped: In the press release, Swift added, "I want to be sure that everyone has the opportunity to come see my show, so we have affordable tickets available for every date we do this year," which equated to a ticket price that started at $20 (plus fees) in many places.

All told, according to Billboard Boxscore statistics, the Fearless Tour grossed $63,705,590 and drew 1,138,977 fans -- meaning Swift had plenty of momentum behind her when her third album, Speak Now, arrived in October of 2010.

PICTURES: Taylor Swift's Best Live Shots

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