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Di Nashville, Swift bekerja dengan penulis lagu berpengalaman Music Row seperti Troy Verges, Brett Beavers, Brett James, Mac McAnally, dan The Warren Brothers.<ref>{{cite news |url=http://www.americansongwriter.com/2011/05/taylor-swift-the-garden-in-the-machine/3/ |title=Taylor Swift: The Garden In The Machine |work=American Songwriter |date=May 2, 2011 |accessdate=May 21, 2012}}</ref><ref name="sonydeal">{{cite web |url=http://www.bmi.com/news/entry/234444 |title=Songwriter Taylor Swift Signs Publishing Deal With Sony/ATV |publisher=[[Broadcast Music, Inc.]] |date=May 12, 2005 |accessdate=April 20, 2012}}</ref> Swift dikontrak oleh [[Sony/ATV Music Publishing|Sony/ATV Tree publishing house]],<ref>{{cite web |last=DeLuca |first=Dan |title=Focused on 'great songs' Taylor Swift isn't thinking about "the next level" or Joe Jon as gossip |url=http://articles.philly.com/2008-11-11/news/25256467_1_big-machine-records-joe-jonas-country-music-association-awards |page=1 |work=Philadelphia Daily News |accessdate=April 17, 2012 |date=November 11, 2008}}</ref> tetapi keluar dari RCA Records ketika berumur 14 tahun.<ref name="albuminfo" />
DisebuahPada sebuah pertunjukan industri di Bluebird Cafe di Nashville pada 2005, Swift menarik perhatian Scott Borchetta, seorang eksekutif DreamWorks Records yang sedang bersiap untuk mendirikan label rekaman independennya sendiri, [[Big Machine Records]]. Dia menjadi orang pertama yang dikontrak, dan ayahnya membeli tiga persen saham diperusahaandi perusahaan baru ini yang bernilai $120,000.<ref name="Taylor in Wonderland">{{cite news|last1=Hiatt|first1=Brian|url=http://www.rollingstone.com/music/news/taylor-swift-in-wonderland-20121025|title=Taylor Swift in Wonderland|work=Rolling Stone|date=October 25, 2012|accessdate=August 1, 2016}}</ref><ref>{{cite news|last1=Greenburg|first1=Zack O'Malley |url=http://www.forbes.com/sites/zackomalleygreenburg/2013/06/26/toby-keith-cowboy-capitalist-countrys-500-million-man/2/ |work=[[Forbes]] |title=Toby Keith, Cowboy Capitalist: Country's $500 Million Man|date=June 26, 2013|accessdate=August 1, 2016}}</ref> Swift mulai bekerja di [[Taylor Swift (album)|debut album yang sama dengan namanya]] tak lama setelah dikontrak. Swift menulis tiga lagu dari album sendiri, dan ikut menulis delapan lainnya dengan penulis Rose, Robert Ellis Orrall, Brian Maher, dan Angelo Petraglia.<ref name="liner">{{cite AV media notes |title=Taylor Swift |others=Taylor Swift |year=2006 |type=CD |publisher=[[Big Machine Records]] |id=BMR120702}}</ref> ''Taylor Swift'' dirilis pada 24 Oktober 2006.<ref name="ibtimes">{{cite news | url=http://www.ibtimes.com/taylor-swift-new-album-release-date-postponed-she-laying-low-after-kim-kardashian-2399940 | title=Taylor Swift New Album Release Date Postponed; Is She Laying Low After Kim Kardashian, Kanye West Drama? | work=[[International Business Times]] | date=August 10, 2016 | accessdate=August 15, 2016 |last=Solin|first=Jennifer}}</ref> ''Taylor Swift'' berada dinomordi nomor lima di [[Billboard 200|''Billboard'' 200]] dan menghabiskan 157 minggu dichartdi chart, membuatnya menjadi album terlama yang berada dichartdi tangga lagu tahun 2000an.<ref>{{cite news|last1=Trust|first1=Gary|title=Chart Beat Thursday: Taylor Swift, Tim McGraw Linked Again|url=http://www.billboard.com/articles/columns/chart-beat/266889/chart-beat-thursday-taylor-swift-tim-mcgraw-linked-again|accessdate=November 8, 2016|work=Billboard|date=October 29, 2009}}</ref>
Big Machine Records masih akan merilis single utamanya, "Tim McGraw", di Juni 2006, dan Swift dan ibunya membantu "memasukkan single CD kedalamke amplop untuk dikirim ke radio".<ref name="EW1">{{cite news |last=Willman |first=Chris |title=Taylor Swift's Road to Fame |url=http://www.ew.com/article/2008/02/05/taylor-swifts-road-fame |work=Entertainment Weekly |accessdate=April 22, 2012 |page=3 |date=February 5, 2008}}</ref> Dia banyak menghabikan waktu di 2006 mempromosikan ''Taylor Swift'' dengan tur radio dan penampilan televisi.<ref>{{cite web|url=http://www.onecountry.com/5-of-taylor-swifts-most-country-performances-1647918372.html|date=November 12, 2014|title=5 of Taylor Swift's Most Country Performances|last=Cowling|first=Lauren|work=Country Outfitter Life|accessdate=August 2, 2016}}</ref><ref name="taylorjoinstour">{{cite web |url=http://www.cmt.com/news/1543489/taylor-swift-joins-rascal-flatts-tour/ |title=Taylor Swift Joins Rascal Flatts Tour |date=October 18, 2006 |publisher=CMT |accessdate=March 11, 2010}}</ref> Mengikuti "Tim McGraw", empat single lain yang dirilis sekitar 2007 dan 2008: "[[Teardrops on My Guitar]]", "Our Song", "Picture to Burn" dan "Should've Said No". Semuanya mendapatmeraih sukses ditanggadi tangga lagu ''Billboard'' Hot Country Songs, dengan "Our Song" dan "Should've Said No" berada dinomordi nomor satu. Swift menjadi orang termuda yang sendirian menulis dan menampilkan lagu nomor satu di chart tersebut.<ref>{{cite web|url=http://www.gactv.com/gac/cda/article_print/0,3008,GAC_26063_5769818_DS-ARTICLE-RIGHT-RAIL,00.html |archiveurl=https://archive.is/20150316163238/http://www.gactv.com/gac/cda/article_print/0,3008,GAC_26063_5769818_DS-ARTICLE-RIGHT-RAIL,00.html |archivedate=March 16, 2015 |title=Taylor Swift No. 1 on iTunes |date=December 19, 2007 |publisher=[[Great American Country]] |accessdate=July 5, 2010 |deadurl=yes |df= }}</ref> "Teardrops on My Guitar" mendapat sukses komersial moderat, berada dinomordi nomor tiga belas di [[Billboard Hot 100|''Billboard'' Hot 100]].<ref name="billboard">{{cite web |url={{BillboardURLbyName |artist=taylor swift |chart=all}}|title=Teardrops on My Guitar|work=[[Billboard (magazine)|Billboard]]|accessdate=December 15, 2010}}</ref> Swift juga merilis album liburan ''Sounds of the Season: The Taylor Swift Holiday Collection'' di October 2007 dan EP ''Beautiful Eyes'' di Juli 2008.<ref name="cst">{{cite web |url=http://www.countrystandardtime.com/news/newsitem.asp?xid=1947 |title=Taylor Swift owns top of country chart |accessdate=December 26, 2008|date=July 23, 2008 |work=[[Country Standard Time]]}}</ref><ref name="gac">{{cite web|url=http://www.gactv.com/gac/nw_headlines/article/0,3034,GAC_26063_5903580_,00.html |archiveurl=https://archive.is/20150316173034/http://www.gactv.com/gac/nw_headlines/article/0,3034,GAC_26063_5903580_,00.html |title=Wal-Mart "Eyes" New Taylor Swift Project |archivedate=March 16, 2015 |accessdate=July 24, 2008 |publisher=Great American Country |deadurl=yes |df= }}</ref> Dia mempromosikan album debutnya secara ektensif sebagai artis pembuka untuk artis lain diturdi tur mereka.<ref>{{cite web|last=Rosa|first=Christopher |url=http://www.vh1.com/news/5861/opening-acts-bigger-than-headliner/ |title=Opening Acts Who Became Bigger Than The Headliner |publisher=[[VH1]] |date=March 24, 2015 |accessdate=November 11, 2015}}</ref>
Swift memenangkan beberapa penghargaan untuk ''Taylor Swift''. Dia merupakan salah satu penerima Nashville Songwriters Association Songwriter/Artist of the Year di 2007, menjadi orang termuda yang pernah diberikan penghargaan tersebut.<ref name=":2">{{cite web|url=http://www.gactv.com/gac/nw_headlines/article/0,,GAC_26063_5723533,00.html |title=Taylor Swift Youngest Winner of Songwriter/Artist Award |date=October 16, 2007 |publisher=Great American Country |accessdate=February 2, 2015 |archiveurl=https://archive.is/20150317154440/http://www.gactv.com/gac/nw_headlines/article/0,,GAC_26063_5723533,00.html |archivedate=March 17, 2015 |deadurl=yes |df= }}</ref> Dia juga memenangkan Country Music Association Horizon Award sebagai Best New Artist,<ref>{{cite web |url=http://www.cmt.com/pictures/taylor-swift/photo-gallery/2389485/2657043/artist_photo.jhtml |title=Photos : All Taylor Swift Pictures : Horizon Award Winner Poses in the Pressroom |publisher=CMT |date=September 7, 2007 |accessdate=May 21, 2012}}</ref> Academy of Country Music Awards Top New Female Vocalist,<ref>{{cite web |url=http://www.cmt.com/pictures/43rd-annual-acm-awards-onstage-winners/1587677/2970629/photo.jhtml |title=Photos : 43rd Annual ACM Awards – Onstage: Winners : Acceptance Speech |publisher=CMT |date=May 18, 2008 |accessdate=May 21, 2012}}</ref> dan [[American Music Awards]] Favorite Country Female Artist.<ref>{{cite web|url=http://www.roughstock.com/blog/taylor-swift-rascal-flatts-carrie-underwood-score-@-2008-ama-awards |archiveurl=https://web.archive.org/web/20140710055906/http://www.roughstock.com/blog/taylor-swift-rascal-flatts-carrie-underwood-score-%40-2008-ama-awards |archivedate=July 10, 2014 |title=Taylor Swift, Rascal Flatts, Carrie Underwood Score at 2008 AMA Awards |publisher=Roughstock.com |type=Blog |date=November 24, 2008 |accessdate=May 21, 2012 |deadurl=yes |df= }}</ref> Dia juga dinominasikan sebagai Best New Artist di [[Grammy Award|2008 Grammy Awards]].<ref>{{cite web |url=http://www.people.com/people/package/article/0,,20173658_20177270,00.html |title=Amy Winehouse Wins Best New Artist, Kanye West Pays Tribute to Mom – Grammy Awards 2008, Grammy Awards |work=[[People (magazine)|People]] |date=October 2, 2008 |accessdate=May 21, 2012}}</ref> DiPada Juli tahun itu, Swift mulai berpacaran dengan [[Joe Jonas]] yang berakhir tiga bulan kemudian.<ref>{{cite web|url=http://www.people.com/people/article/0,,20230694,00.html |title=Scoop |last=Caplan |first=David |date=September 8, 2008 |work=People |accessdate=March 6, 2012 |archiveurl=https://web.archive.org/web/20160202044308/http://www.people.com/people/article/0%2C%2C20230694%2C00.html |archivedate=February 2, 2016 |deadurl=yes |df= }}</ref><ref>{{cite web|url=http://www.people.com/people/article/0,,20245498,00.html |archiveurl=https://web.archive.org/web/20160303204136/http://www.people.com/people/article/0%2C%2C20245498%2C00.html |archivedate=March 3, 2016 |title=Scoop – Couples, Camilla Belle, Joe Jonas |last=Rizzo |first=Monica |date=November 24, 2008 |work=People |accessdate=March 6, 2012 |deadurl=yes |df= }}</ref>
=== 2008–2010: ''Fearless'' dan akting ===
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