Taylor Swift's Career Timeline: From 'Tim McGraw' to '1989'

Taylor Swift releases her self-titled debut album on Big Machine Records. Taylor Swift debuts at No. 19 on the Billboard 200, holding a position on the Chart for 277 weeks and peaking at No. 5.

Swift releases "Teardrops On My Guitar," the second single off her debut album. "Teardrops" stays on the Billboard Hot 100 for 48 weeks, peaking at No. 13.

"Our Song," the third single from Swift's debut album, is released. The track spent a total of 36 weeks on the Billboard Hot 100, peaking at No. 16. It also becomes her first No. 1 on the Hot Country Songs chart, spending six weeks atop the list.

Swift releases her first EP, Sounds of the Season: The Taylor Swift Holiday Collection, on Big Machine Records. The EP peaks at No. 20 on the Billboard 200 and at No. 1 on Top Holiday Albums.

Taylor Swift dates Joe Jonas. The Jonas Brother infamously breaks up with Swift over a 27-second phone call and reportedly inspires her songs "Last Kiss," "Forever and Always," and "Holy Ground."

"Love Story," the lead single off of Taylor Swift's second studio album Fearless, is released. The track spends 36 weeks on the Billboard Hot 100, peaking at No. 4, and hits No. 1 on Hot Country Songs.

Swift’s single “Love Story” is named song of the year at BMI’s 57th Country Awards, making it Swift’s second consecutive win in the category following her 2008 win for “Teardrops on My Guitar.”

Fearless, Swift's second studio album, is released by Big Machine Records. The album held the No. 1 position on the Billboard 200 for a total of 11 non-consecutive weeks, becoming the longest chart-topper by a female country artist.

Taylor Swift makes her debut appearance as a musical guest on Saturday Night Live. She returns on Nov. 7, 2009 as both host and musical guest.

The singer performs her song "Fifteen" with Miley Cyrus at the 51st Grammy Awards. Swift goes on to win a total of seven Grammy Awards between 2009 and 2012.

Taylor Swift's single "You Belong With Me" becomes her fourth No. 1 on the Hot Country Songs chart and her highest-charting hit, at the time, on the Billboard Hot 100, reaching No. 2.

Taylor Swift and Taylor Lautner date after meeting on the set of the romantic comedy Valentine's Day. Lautner is speculated to have inspired Swift's song "Back to December."

Taylor Swift receives the award for best female video at the 2009 MTV Video Music Awards. During her acceptance speech, Kanye West infamously takes the stage to interrupt. "Yo, Taylor, I'm really happy for you, I'ma let you finish, but Beyonce had one of the best videos of all time!" he exclaims. "One of the best videos of all time!"

Taylor Swift has a brief romance with John Mayer, who's 13 years her senior. Mayer reportedly inspires Swift's song "Dear John" from the album Speak Now.

Taylor Swift's third studio album Speak Now is released on Big Machine Records. The album peaked at No. 1 on the Billboard 200 for 11 non-consecutive weeks, becoming the best-selling album of 2009 in the U.S., according to Nielsen SoundScan.

The singer wins artist of the year at the American Music Awards.

The singer graces the cover of fashion bible Vogue.

Then-22-year-old Swift begins dating 18-year-old Conor Kennedy. Kennedy is believed by some to have inspire Swift's song "Begin Again."

Taylor Swift releases "We Are Never Ever Getting Back Together," the lead single off of her fourth studio album, Red. The single becomes the first in Swift's career to peak at No. 1 on the Billboard Hot 100.

The singer's fourth studio album, Red is released on Big Machine Records. The album sold 1.21 million copies in its first week in the U.S. and debuted at No. 1 on the Billboard 200 chart, making it the second-highest debut for a female artist (after Britney Spears' Oops!...I Did It Again).

Taylor Swift dates One Direction's Harry Styles. While opening the 2013 Grammy Awards with her single "We Are Never Ever Getting Back Together," Swift takes a jab at Styles by using a fake British accent during the spoken portion of the song.

Taylor Swift wins artist of the year for the third time at the American Music Awards, making her the all-time winner in the category.

The Red Tour starts in Omaha, Neb. During a stop on the tour in Sydney, Australia, Swift sells out the Allianz Stadium (with an at-capacity crowd of 40,900 fans), making her the first female artist in history to do so since it opened in 1988. She was also the first female artist since Madonna to undertake a stadium tour Down Under.

"I Knew You Were Trouble" wins best female video at the 2013 MTV Video Music Awards.

Swift releases the single "Shake It Off," the first single off of her fifth studio album 1989.

Days after performing it on the MTV VMAs (pictured), "Shake It Off" becomes Swift's second Billboard Hot 100 No. 1, and just the 22nd title to debut at No. 1 in the chart's five-decade history.

Taylor Swift's 1989 debuts at No. 1 on the Billboard 200 albums chart with the largest sales week for an album since 2002. 1989 sold 1.287 million copies in the week ending Nov. 2, according to Nielsen SoundScan. 1989 is Swift’s fifth studio album and was released Oct. 27 through Big Machine Records.

“Blank Space” hits No. 1 on the Billboard Hot 100, giving the 1989 album its second chart-topper. It would spend a total of seven weeks at No. 1.

The bow of Swift's epic star-studded video for “Bad Blood” (which premiered on the Billboard Music Awards) helps lift the song to No. 1 on the Billboard Hot 100.

The 1989 album celebrates a full first year in the top 10 of the Billboard 200 chart, making it just the fifth album to spend its first 52 weeks of release in the top 10.

“Wildest Dreams” climbs to No. 5 on the Billboard Hot 100, giving the 1989 album its fifth top 10 single.

Swift tops Billboard's Dance/Mix Show Airplay chart for the first time, with "Wildest Dreams." The song rules the tally thanks in large part to an officially commissioned remix by DJ R3hab.

Swift takes home three 2015 Grammy Awards, for best music video ("Bad Blood"), best pop vocal album (1989) and album of the year (1989). She's the first woman to win the album of the year award twice for their own album. She previously won the award for Fearless.

"Out of the Woods" becomes the sixth top 20-charting single from 1989 on the Pop Songs airplay chart. It peaks at No. 12.

1989 spins off a seventh top 20-charting hit on the Pop Songs chart with "New Romantics," as the song peaks at No. 18.

Swift wins her 21st career Billboard Music Award, for top touring artist. Through 2016, she has earned 21 Billboard Music Awards -- the most of any artist.

The entertainer celebrates the 10th anniversary of her debut on Billboard's charts: "Tim McGraw" debuted on the July 1, 2006-dated Hot Country Songs chart at No. 60.

Swift scores her 20th top 10 Billboard Hot 100 hit, as "I Don't Wanna Live Forever (Fifty Shades Darker)," with Zayn, debuts at No. 6; it goes on to peak at No. 2. She's the sixth solo woman in the Hot 100's history to tally at least 20 top 10s, following Madonna, Rihanna, Mariah Carey, Janet Jackson and Whitney Houston.

"Look What You Made Me Do," the lead single from Swift's album Reputation, vaults 77-1 on the Billboard Hot 100 (following its first full week of data tracking), becoming her fifth No. 1 on the list.

Swift's Reputation launches as her fifth No. 1 album on the Billboard 200. Starting with 1.2 million sold in its first week, the sum marks her fourth million-selling week for an album, making her the first artist in Nielsen Music history to achieve four million-selling frames.

Having gone all-out pop in 2014 on her album 1989, after breaking through as a country superstar, Swift makes her first visit to the Hot Country Songs chart in nearly four years, as ballad "New Year's Day," from her album Reputation, debuts at No. 40. Swift totaled 19 top 10s, including seven No. 1s, on Hot Country Songs from her chart arrival in 2006 through 2013.
 

For the full list of Swift's 40 biggest Billboard chart hits, click here.

After announcing that "Delicate" would be the sixth single from Reputation, the track debuts on the Billboard Hot 100 chart (dated March 24) and reaches No. 46 a month later. The song becomes her 76th entry on the chart, which passes Ray Charles for 10th-most entries in the Hot 100's 60-year history.