Mary Chapin Carpenter began to achieve commercial recoginition with the 1989 release of her second album, State of the Heart, which Jack Hurst of the Chicago Tribune (November 5, 1989) called a "a knockout punch to any doubts that an Ivy Leaguer can aspire to major-league stature in the field of Reba McEntire." Coproduced by Carpenter, State of the Heart features songs that are shorter and less introspective than those on ther first effort. The first single from the album, the rowdy "How Do," was the first of her songs to be played on commerial radio, and it climbed to number nineteen on the Billboard country charts. The collection's second single "Never Had it so Good," which reached number eight on the country charts, revolves around a strong female character, as do many of Carpenter's songs.

State of the Heart not only remained on the country charts for sixty-four weeks but also broke through onto the pop charts, reaching number 180. A critical as well as a popular success, State of the Heart earned a place on many magazines' year-end best list, including that of CD Review, which named it one of the top three country records of the year. That magazine's music editor also chose it as one of his five favorite albums of the year from any category. In 1990 Carpenter won an Academy of Country Music (ACM) award for best new female vocalist, and her song "Quittin' Time," about the end of a long relationship, was nominated for a Grammy for best female vocal performance in the country category. In the same year, she was again the star of the Wammies, walking away with nine awards.

Her suburban background and the widespread appeal of her music notwithstanding, by the early 1990's Carpenter was on the way to being pigeon-holed as a country musician. "I was just a singer/songwriter," she told Clark Parsons of Nashville Scene (April 15, 1993). "If anyhthing, I felt insecure about fitting into any kind of category. Not because I didn't want to be part of any category, but that I thought that somebody was going to find me out and say, 'You don't belong here. You're a fraud.' Then somebody called me a country musician, and I was scared. I felt like I was credential-poor, but my heart was in the right place." Any doubt about Carpenter's credentials were erased in October 1990 with the release of her third album, Shooting Straight in the Dark, a collection of songs about coming to terms with aging and dealing with relationships. The album contains some of her most personal lyrics, in such songs as "Can't Take Love for Granted," "What You Didn't Say," "When She's Gone," "Middle Ground," and "You Win Again."

Carpenter career got an unexpected boost when she was invited to perform at the 1990 Country Music Association (CMA) award show. A last-minute addition to the roster of stars scheduled to appear, Carpenter was asked by the show's producer, Irving Waugh, to perform an unrecorded song called "The Opening Act," a tongue-in-cheek account of the sometimes unpleasant experiences associated with serving as an opening act for more established artists. Afraid that the song's lyrics might offend some of the country music veterans in the audience, Carpenter at first declined the invitation, but she eventually relented and performed the number. To her amazement, the tough industry crowd rose to its feet and gave her a standing ovation. Almost overnight she became a house-hold name in the music industry, resulting in appearances on Late Night with David Letterman and CBS This Morning and feature stories in publications ranging from Cosmopolitan to the Wall Street Journal.

Carpenter spent most of 1991 touring to promote her album. Although her critically acclaimed shows are sellouts, she is not entirely comfortable onstage. "It's always a battle of nerves," she told Paul Freeman for a May 1993 Los Angeles Times article. " I have to find a level of control within myself. Once I do, I have a great time." She was nominated in 1991 for the CMA's prestigious Horizon Award, which honors artists who have demonstrated significant growth over the year, and by the ACM, for best female vocalist. Although she failed to win either award, the nominations signaled that she was gaining acceptance among country musicians.

In 1992 Carpenter received Grammy nominations for best country song and best country female vocal performance, for "Down at the Twist and Shout," a rousing number from Shooting Straight in the Dark. A tribute to the defunct Twist and Shout club, in Bethesda, Maryland, the cajue flavored rockabilly song stands apart from the introspective ballads that dominate the album. Carpenter and her band, augmented by members of the cajun band Beausoleil, performed "Down at the Twist and Shout" at the February 1992 Grammy Awards ceremony, at which Carpenter was presented with the statuette for best country female vocal performance. She also earned ACM nominatons for top female vocalist and song of the year, for "Down at the Twist and Shout".

Come On Come On, became Carpenter's fourth album and features guest appearances by Shawn Colvin, the Indigo Girls, and Rosanne Cash and includes songs written by Mark Knopfler of the rock band Dire Straits ("The Bug"), and Lucinda Williams ("Passionate Kisses). Described by Karen Schoemer of the New York Times (August 9,1992) as "a testament to the woman who don't usually make headlines," it went gold (five hundred thousand copies sold) within thirty days of its June 1992 release, plantinum (one million copies sold) six months later, and double pltinum (two million copies sold) in early 1994. In September 1992 Carpenter received her first CMA award, for female vocalist of the year, and at the 1992 Wammies she took top honors for song, video, and album of the year. The single "He Thinks He'll Keep Her" reached the top of the country charts, and Come On Come On landed on the year-end best lists of numerous publications, including Rolling Stone, Billboard, Spin, the New York Times and Entertainment Weekly, among others. Carpenter capped off the year by performing at the star-studded tribute to Bob Dylan at Madison Squared Garden, in New York City. Together with Rosanne Cash and Shawn Colvin, she captivated the crowd with a rendition of Dylan's "You Ain't Goin' Nowhere."

In 1993 Carpenter won her second Grammy for best country female vocal performance, for the song "I feel Lucky", about a woman who stays home from work, wins the lottery, and ends up being wooed by country stars Dwight Yoakam and Lyle Lovett. She also received the Academy of Country Music award for female vocalist of the year, and she was nominated for a prize in three other categories: best album, best single ("I Feel Lucky"), and, for "Not Too Much to Ask", which she sang with Joe Diffe, best vocal duet. At the 1993 CMA awards, she captured her second consecutive trophy for best female vocalist. After spending most of eighteen months on the road, in late 1993 Carpenter decided to take a year off from touring. Nevertheless, Come On Come On continued to sell well two years after its release, and the song "Passionate Kisses" earned her a third straight Grammy for best country female vocal performance, in 1994. In October 1994 she released Stones in the Road, a collection of original songs, coproduced by Carpenter and her longtime collaborator and guitarist John Jennings.

Stones in the Road, which sold more than a million copies in it's first few weeks, is Carpenter's most personal album to date, a moody, sometimes dark vision that is both intimately personal and expansively universal. "Most of Stones in the Road's wool-gathering themes revolve around unusually complex issues-not just loss of love, but even trickier and murkier dilemmas regarding personal ethics and personal insecurity", reported Bob Allen in Country Music (May/June1995). As Carpenter explains, these are all issues she's had to grapple with during the past few giddy, tempestuous years, a watershed period which she sometimes refers to as her "baptism by fire." Carpenter says in the interview, "I'm reluctant to make it sound like, 'Poor me,' like I'm complaining, because I've got a dream job, ya know, but I certainly felt a couple of years ago, when I decided to get off the road for a while and start writing the songs for Stones in the Road, that I was a real fry baby. My personal life was crummy-I really didn't have a life. It was mostly that I hadn't learned to take the time for myself that I really needed to take; I hadn't discovered that it was within my power to do that."

Carpenter has said that Stones in the Road wasn't an easy record to make. Although she wrote steadily in the year after she came off the road from Come On Come On, she wasn't happy with the songs. "I worked on it for about a year, but I just didn't like what I was doing, I was certainly producing but it just didn't seem to float my boat. What I was writing lacked meaning or a trueness." The break came after she wrote "John Doe No.24," a harrowing, beautiful song about a deaf-mute found wandering on the streets of Jacksonville, Ill., in 1945. John Doe 24 is a real person whom Carpenter discovered after reading his obituary in a newspaper. Writing the song opened the creative floodgates and the rest of the record came in a rush. "Once I finished 'John Doe," I felt like I've got these tools back and they're working for me, from there it was like chapter came after chapter. I'm not a prolific writer; I don't churn things out, so that was a very euphoric time for me, to feel so kind of full and brimming and being able to work constantly, to work for long periods of each day and feel satisfied." In March 1995, Carpenter picked up two more Grammy's. She won her fourth consecutive Best Country Vocal Performance Female (an unprecedented feat), and Stones in the Road won the newly created Best Country Album.