Lydia Loveless performing at
 SXSW 2014


 In 2004, Loveless, their father, and their sisters made up part of a four-member new wave pop band called Carson Drew, named after the father in the Nancy Drew books. Loveless played bass. The band broke up in 2007.


At a show in Cincinnati where they opened for his band, Loveless met producer David Rhodes Brown (500 Miles to Memphis) who went on to produce their first album, 2010's The Only Man. Loveless was not happy with the slick production of the album. Loveless made the record when they were 15 years old. Loveless clarified that they like the songs they wrote, but the drawn-out process (over three years) to get the album released influenced their feelings about the project.


Columbus attorney Steve McGann became their manager. Loveless and their band drove 20 hours to Austin, Texas, and ended up playing for Bloodshot owners Rob Miller and Nan Warshaw at the 2010 South by Southwest music festival.


In 2012, signed with Bloodshot and determined to make a more raw and edgier album, they released Indestructible Machine with songs that feature themes of frustration with their hometown, drinking, depression, and a humorous song about being stalked by a man who referred to himself as Steve Earle but was not in fact the singer of "Copperhead Road". Loveless recorded the album with many live takes and a minimum of overdubs at Grove City, Ohio's Sonic Lounge recording studio with engineer Joe Viers. Spin characterized the record as standing out "for its utter lack of bullshit", with "roaring vocals, in her narrators' lived-in-bars recklessness, and in her overall inability to mince words."


Indestructible Machine received praise from AllMusic and in publications such as the Chicago Tribune, Spin, and The Washington Post. Greg Kot wrote that Loveless' "defiant tone is matched by songs that put country and punk on equal ground, unvarnished and direct".


In the Spring of 2013, Loveless did an extensive Canadian tour supporting the Supersuckers. Loveless and their band also toured Scandinavia and Spain during the fall of 2013.


Lydia Loveless singing Four Leaf
Clover with the Old 97s. 9:30 Club
(Washington DC)
May 31, 2014

In 2013, Loveless released Boy Crazy, an EP. Mark Deming of AllMusic praised the release, asserting that the album "is further proof that Loveless is a major talent, and if her next album is as good as this, she may run the risk of becoming a very big star". One of the songs, "Lover's Spat", is about the serial killer Jeffrey Dahmer.

Rolling Stone cited Loveless as one of its "10 New Artists You Need to Know: January 2014".

In February 2014, Loveless released their third full-length record, Somewhere Else, on Bloodshot Records, which has a dark, "poppy" vibe. Stereogum said Loveless is using their "unmistakable voice as a songwriter, and she's only getting better at using it to blur the line between running her mouth and pouring out her heart." Loveless was listed as one of "5 Best New Artist for January 14" by Spin magazine. The record includes "Head", a single Loveless wrote with their guitar player, Todd May, a fellow songwriter. The album had a very positive reception and entered Billboard's Heatseekers chart (new entries to Billboard charts, compiled by Nielsen SoundScan) the first week of its release at position number 7.

In April 2014, Loveless released the Mile High/Blind 7" record for Record Store Day. The record had a non-album cut titled "Mile High" on the A side and a cover of Kesha's "Blind" on the B side. It was a limited edition release on lime green vinyl. The tracks were released in digital album format on May 27, 2014.

In April 2015, Loveless was part of a Record Store Day release with label-mate, Cory Branan. The two artists cover two Prince songs: Loveless doing "I Would Die 4 U" and Branan doing "Under the Cherry Moon". The 7" limited edition releases were also pressed onto purple vinyl.

Loveless donated their vocal talent to the end credits song from the film, A Dog Named Gucci, in the song "One Voice", which also features the voices of Norah Jones, Aimee Mann, Susanna Hoffs, Neko Case, Brian May and Kathryn Calder. It was produced by Dean Falcone, who also wrote the film's score. "One Voice" was released on Record Store Day, April 16, 2016, with profits from the sale of the single going to benefit animal charities.

In August 2016, Bloodshot Records released their third studio album, Real. Their first ever music video, for the album's first single "Longer" received its world premiere through Rolling Stone in July 2016. The video was directed by filmmaker Gorman Bechard, who directed the documentary on Loveless. On August 19, a second Bechard-directed music video was released this time for the song "Clumps". The next morning Loveless and their band made their American TV network debut, performing three songs on CBS Saturday Morning. A video for the song "European", also directed by Bechard, debuted in November 2016.

The A.V. Club called Real "an adventurous, brutal honest sucker punch", while The Boston Globe said, "Loveless continues to manifest a remarkable combination of bruised vulnerability and desperate longing, alongside a tough, self-deprecating resilience, but there's more of the former and less of the latter this time. She's still preoccupied with the downsides of love: longing for something you don't (or can't) have, the inevitable dissolution of whatever you manage to find (and the difficulty of finding it in the first place), and the emotional pitfalls of navigating it." Rolling Stone liked the shift in genre towards a more pop sound.

Loveless released their fourth studio album Daughter through their own label, Honey, You're Gonna Be Late Records on September 25, 2020.