Additionally, Ashford is known for portraying the role of Betty DiMello on the Showtime American period drama television series Masters of Sex, which ran for four seasons on Showtime.
Ashford was born in Denver, Colorado, and raised by her mother, Holli Swanson, an elementary school gym teacher and her father Chris Swanson, a small business owner. Ashford participated in Kids Cross Country and Track at the age of six, coached by her mother. It was discovered there that she hated running, and it was very clear that she was more interested in the costume for the races rather than the actual races themselves. The last race she ever ran was the 400 metres. After that race, her mother decided it was time to enroll her in the nearest dance studio. She was first enrolled and started studying at Kit Andrée's Dance and Performing Arts Center the same day she started the second grade. She acted and sang in numerous performances in her hometown, including the leads in the musicals Ruthless!, and Anything Goes. She graduated from Wheat Ridge High School in three years at the age of 16, and then attended Marymount Manhattan College, where she earned a degree in theatre in another three years at the age of 19. Ashford's professional career began at age nine, when she was cast as the lead in Ruthless! at "Theatre on Broadway". At fourteen, she was profiled as "The Teen to Watch" by the Rocky Mountain News.
In 2004, while hanging around in New York City's Lower East Side club scene, Ashford met nightlife personality Lady Starlight, a local rock DJ and performance artist. Lady Starlight invited the budding starlet to dance at her 1970s glitter rock party "Lady Starlight's English Disco", and christened her Hollywood Starr. She performed in Tom Kitt and Brian Yorkey's Feeling Electric as Natalie at the New York Musical Theatre Festival in 2005.
Soon after graduating from college, Ashford got her big break performing as one of Glinda's friends, Pfanne, and understudying the role of Glinda on the First National Tour of Wicked. She joined the cast in December 2005 and left in September 2006. She then originated the role of Margot in Legally Blonde: The Musical, her Broadway debut. She also understudied the lead role of Elle Woods, but only went on once. She was featured on the original cast recording and appeared in the MTV televised airing. She left the show in September 2007.
In July 2007, she worked on a musical adaptation of Catch Me if You Can as Brenda Strong. She previously did a staged reading for the project under the Tony Award-winning director of Hairspray, Jack O'Brien.
She then returned to Wicked, this time playing the lead role of Glinda in the Broadway production. She replaced Kendra Kassebaum on October 9, 2007. She departed the company on May 11, 2008 when Kassebaum returned to the role, and transferred to the Chicago production, replacing Kate Fahrner as Glinda on June 3, 2008. She played her final performance as Glinda on January 25, 2009, when the Chicago production closed.
In 2008, she made her film debut with a small part in Sex and the City: The Movie playing a "spoiled label queen". She also appeared in the film Rachel Getting Married as a counter girl.
In August 2008, Ashford played Wednesday Addams in the staged reading for musical adaptation to The Addams Family with Nathan Lane and Bebe Neuwirth, but she was later replaced by Krysta Rodriguez. Other readings include Bring It On: The Musical as Campbell, The Black Suits, C'mon Get Happy, Pal Joey, and a gender bent version of Stephen Sondheim's Company.
In 2009 it was announced that Ashford would take place as one of the principal characters and singers in the new vaudeville styled Cirque du Soleil show, Banana Shpeel. However, even following a national television broadcast on America's Got Talent, it was announced that Ashford and her colleague, Michael Longoria, were no longer in the cast of the show. Publicists announced that the two leading vocalists had fallen victims of a creative decision to remove large portions of dialogue from the show, therefore making their characters non-existent. Ashford was originally slated to stay in the production from its premiere in Chicago until sometime in 2010.
Ashford starred as Jeanie in the Broadway revival of Hair. She succeeded Kacie Sheik in the role from March 9, 2010 through June 27, 2010 when the production closed.
In September 2010, Ashford made her directorial debut at Birdland Jazz Club, directing fellow Hair alum Jay Armstrong Johnson in his solo concert debut. The concert was met with rave reviews, including a notice for Ashford's "thoughtfully put together" directorial style.
In September 2010, Ashford played Veronica Sawyer in a concert in New York City of the new musical Heathers. The role was later played in the 2014 off-Broadway premiere by Barrett Wilbert Weed.
In November 2010, Ashford was part of a reading of the musical Carrie. In December 2010, she participated in a "creative workshop" reading of the stage musical version of Diner, as Beth.
In January 2012, Ashford ended her run playing Maureen Johnson in the Off-Broadway revival of Rent, which began July 14, 2011 and closed on September 9, 2012. Emma Hunton took over the role of Maureen from her on January 13, 2012. In February 2012, Ashford made a cameo on Smash as Lisa McMann, and returned for another short appearance in 2013 before cancellation.
From June 27 to August 19, 2012, she appeared in the Off-Broadway musical Dogfight, based on the 1991 film of the same name, playing a toothless hooker named Marcy. The role in the film was originally played by Elizabeth Daily.
In 2013, Ashford provided the voice of a troll in the highest grossing animated film of all time, Frozen. She has a short line greeting Kristoff, and sings the second female solo after Maia Wilson in the song 'Fixer Upper' for the soundtrack.
In 2013, after first appearing in the Chicago try-outs, she reprised her role as Lauren in the Broadway production of Kinky Boots, a musical with a book by Harvey Fierstein and music and lyrics by Cyndi Lauper. For this role, Ashford received nominations for the Tony Award for Best Featured Actress in a Musical and the Drama Desk Award for Outstanding Featured Actress in a Musical. Ashford left her role in Kinky Boots on March 2, 2014.
In 2013, Ashford appeared in the recurring role of young prostitute Betty DiMello in season one of the Showtime series Masters of Sex. Her part was upgraded from a recurring to regular for season two.
On January 14, Ashford released her first single, "Another Time (Andrew's Song)", with musical director Will Van Dyke on iTunes. In addition to writing music and lyrics, Van Dyke is the featured pianist on the single. The track also features Michael Aarons on guitar, Steve Gilewski on bass, Sammy Merendino on drums, Philip Payton on violin/viola, and Allison Seidner on cello. It was recorded at Harlem Parlour Recording, NYC by Derik Lee, who also mixed and mastered the recording.
Beginning on August 26, 2014, Ashford played the role of Essie Carmichael in the Broadway revival of You Can't Take It with You, directed by Scott Ellis. She appeared alongside Rose Byrne, James Earl Jones, and Elizabeth Ashley. The show closed on February 2, 2015. For this role, she won the 2015 Tony Award for Best Featured Actress in a Play.
In a limited run from October 2, 2015 to January 3, 2016, Ashford starred as the titular canine in the first Broadway production of Sylvia by A.R. Gurney. The show opened at the Cort Theatre on October 27, 2015. Directed by Daniel J. Sullivan, the show also starred Julie White, Matthew Broderick and Robert Sella.
Ashford's debut album was released on November 13, 2015.
On November 17, 2015, it was announced that Ashford had signed with talent agency ICM Partners.
On November 20, 2015, BroadwayWorld.com announced that Ashford would be the involved in a filmed career retrospective Q&A with SAG-AFTRA, taking place on December 3, 2015 at The New School. The Q&A was released via YouTube on December 14, 2015.
On November 20, 2015, Ashford was selected to present the sixth annual Clive Barnes Theatre Award, taking place on January 11, 2016.
On November 30, 2015, Ashford played eight various roles in a reading of Paul Rudnick's critically acclaimed play Jeffrey, directed by Christopher Ashley. Other cast included Michael Urie, Robin de Jesus, James Monroe Iglehart, Andrew Keenan-Bolger and Russell Tovey.
On February 1, 2016, it was announced that Ashford would be taking on the live-in groupie Columbia in the FOX television remake of The Rocky Horror Picture Show.
On July 14, 2016, it was announced that Ashford would be starring opposite Jake Gyllenhaal in New York City Center's Sunday in the Park with George as Dot/Marie, a role originated by Bernadette Peters on Broadway.
On December 13, 2016, it was announced that Ashford would reprise her role as Dot/Marie opposite Gyllenhaal in Sunday in the Park with George in the show's Broadway revival at the Hudson Theater. Ashford was not eligible for a Tony Award for this performance, as the production withdrew itself from any award competition, including the Tony Awards. A statement was released on February 3, 2016 saying: “The producers of Sunday in the Park with George will not be submitting Hudson Theatre’s engagement of this New York City Center production for awards eligibility. With a season so full of tremendous, soon-to-be long-running new musicals and revivals, the producers feel this extremely limited, special run stands most appropriately outside of any awards competition. The production is nevertheless proud to be part of such a landmark Broadway season.”
On April 4, 2017, it was announced that Ashford would be joining The Public Theater's Shakespeare in the Park production of A Midsummer Night's Dream as Helena.
On April 20, 2017, it was announced that the revival of Sunday in the Park with George would be preserved on an album to be released by Warner Music Group. The cast recording, produced and mixed by Bart Migal, will include the full Broadway company, including Jake Gyllenhaal, Robert Sean Leonard, Erin Davie, and Penny Fuller.
On April 28, 2017, Ashford was seen filming on the set of The Assassination of Gianni Versace: American Crime Story. On June 21, 2017, it was announced through Entertainment Weekly that Ashford would portray Elizabeth Cote in the series, which is set to air in 2018.
Sources:2007: Legally Blonde (Original Broadway Cast Recording)
2013: Dogfight (Original Cast Recording)
2013: "Love Me Back" – single (with Richard Hall)
2013: "Stand Beside Me" – single (with Richard Hall)
2013: Kinky Boots (Original Broadway Cast Recording)
2013: Frozen (Original Motion Picture Soundtrack)
2014: "Another Time (Andrew's Song)" – single (with Will Van Dyke)
2014: Ahrens & Flaherty: Nice Fighting You (A 30th Anniversary Celebration Live at 54 Below)
2015: Lost in the Stars: Live at 54 Below
2016: The Rocky Horror Picture Show: Let's Do the Time Warp Again
2016: "A New Year" – single (with Will Van Dyke & Jeff Talbott)
2017: Sunday in the Park with George (2017 New Broadway Cast Recording)
On April 7, 2008, Ashford made her professional cabaret debut as a part of the Broadway at Birdland series at Birdland Jazz Club. She performed an early version of what has now become her critically acclaimed Lost in the Stars show. Many songs from her debut, including Love Hurts, Mona Lisas And Mad Hatters, and the titular song, Lost in the Stars, stayed with the show and are now featured on her live album. Alex Lacamoire served as her musical director.
In February 2014, Ashford made her 54 Below concert debut with her now acclaimed cabaret show, Lost in the Stars. After two sold-out shows on the 3rd of the month, Ashford added an encore performance due to popular demand. She returned to 54 Below for a special Christmas themed reincarnation of her cabaret act for the first two Mondays of December with "a little more holiday cheer involved". She was reviewed by Stephen Holden of The New York Times for her show on December 1. On February 11, 2015, it was announced that Ashford will be joined by Van Dyke and The Whiskey Five band in a tour of her acclaimed cabaret show in five cities. In addition to her February 11 return to 54 Below, she also played in Chicago, San Francisco, Las Vegas, and two special shows in her hometown of Denver, Colorado.
On August 30, 2015, Ashford had a secret popup concert at 54 Below entitled Brunch With Annaleigh: The Concert, which was an extension of the Lost in the Stars show. This concert was recorded to serve as part of Ashford's debut album, which is a compilation of multiple New York City dates at 54 Below in 2014 and 2015.
On September 29, 2015, it was announced that Ashford's debut album, Lost in the Stars: Live at 54 Below, a live recording of her Lost in the Stars show, would be released on November 13, 2016.
Ashford returned to 54 Below for a New Year's Eve edition of her Lost in the Stars show entitled Lost in the Stars: New Year's Magic. The concert also served as an album release party. On November 26, 2015, Lost in the Stars was nominated for a 2015 BroadwayWorld Cabaret Award in the category "Best Show, Celebrity Female". On September 13, 2016, it was announced that Ashford would once again return to 54 Below for an updated version of the New Year's Eve edition of her Lost in the Stars show, Lost in the Stars: New Year's Magic.
Ashford has celiac disease, and because of this, maintains a strict gluten-free diet. Ashford and fellow actor Joe Tapper were married at the Devil's Thumb Ranch in Tabernash, Colorado on July 29, 2013. On May 11, 2016, People announced that Ashford and Tapper were pregnant with their first child, a boy. Ashford and Tapper's son, Jack Clark Tapper, was born on September 8, 2016.