A Trisha Yearwood Retrospective, Part Five: 2000-2002

A Trisha Yearwood Retrospective

Part Five: 2000-2002

Trisha Yearwood makes two of her best albums before heading on the first hiatus of her career.


“Real Live Woman”

Written by Bobbie Cryner


Country #16 | Pop #81

Grade: A

Bobbie Cryner may not have written many songs in her all too brief career, but the ones she did demonstrated that she was among the strongest singer-songwriters of her generation. Cryner stuck a demo of “Real Live Woman” in Yearwood’s mailbox, and Yearwood later noted that when she saw the title, she hoped the song was as good as that title indicated.

It was. “Real Live Woman” is a statement of body positivity and the right of a woman to take up space in general.  At the time, it felt very of the moment.  22 years later, it has a greater urgency, as women are under attack in a way that I’ve never seen in my lifetime.  

Having the greatest vocalist of her generation sing that “I no longer justify reasons for the way that I behave” and “I offer no apologies for the things that I believe and say” was a statement of solidarity in 2000.  In 2022, it’s a manifesto.  – Kevin John Coyne


Real Live Woman


United States:

Country #4 | Pop #27


UK #79

Track Listing:

Where Are You Now

One Love

Sad Eyes

Some Days

I Did

Try Me Again

Too Bad You’re No Good

Real Live Woman

I’m Still Alive

Wild For You Baby

Come Back When it Ain’t Rainin’

When a Love Song Sings the Blues

International Edition Also Includes:

You’re Where I Belong

Something So Right

By 2000, Trisha Yearwood had already proven herself a singular, generational talent and one of the few country stars of her era who was truly an “albums” artist. She’d already dropped one outright masterpiece with Hearts in Armor, her sophomore effort, which followed the dissolution of her first marriage. On the heels of another divorce, she dropped her second masterpiece, Real Live Woman

What’s most striking about the collection is the depth of the interior lives of the narrator on every song: The women Yearwood inhabits on this album, to a one, scan as very real and very much alive. That’s a direct reflection of both the songwriters whose catalogs Yearwood plumbed for this set– Matraca Berg and Kim Richey remained two of her go-tos, while she also gave overt nods to key influences Linda Ronstadt and Bruce Springsteen– and of Yearwood’s extraordinary performances. 

She nailed opener “Where Are You Now” to the wall, giving one of the most torrid vocal turns of her career to a song fully worthy of such overt power, and she exudes confidence in her agency as an adult woman on the title track, a stunning and forward-thinking song written by the brilliant Bobbie Cryner. There’s a deep sadness to her rendition of Ronstadt’s “Try Me Again,” and that emotion peaks later as she sings of her tears falling onto her piano keys on “When a Love Song Sings the Blues.”

On any given day, Real Live Woman would be my pick for Yearwood’s finest album, no mean feat when considering that we’ve already covered Hearts in Armor and have at least one more true masterpiece yet to come. That the album refocused Yearwood’s career after her only fallow era certainly marks it as her most pivotal album, in addition to being one of her absolute best. –  Jonathan Keefe


“Where are You Now”

Written by Mary Chapin Carpenter and Kim Richey



Grade:  A

The best single of Yearwood’s storied career, and she made a career full of brilliant singles. Quite simply, “Where are You Now” is a flawless showcase for Yearwood’s song sense and her understanding of how to deliver a great song with a nuanced and sophisticated vocal performance. 

The way she stretches out “now” going into the second chorus.  The way she hits a range of high notes singing “used to be” in the bridge.  The three part harmony with Mary Chapin Carpenter and Kim Richey that was as good as anything on the best Chicks record. The way she knew to get out of the way and just do a straight delivery of the best couplet in her catalog: “I’m good one of a kind, but I would rather be two/And I still speak my mind, but I miss talking with you.” 

Everything about “Where are You Now” is perfect. That country radio ignored it was an ominous harbinger for the way women would be sidelined completely by the middle of the new decade.  – KJC


“Sad Eyes”

Written by Bruce Springsteen


U.K. Single (Did Not Chart)

Grade: B+

Bruce Springsteen’s “Sad Eyes” had been covered before, and his original version is a great listen, too.  But none of the recordings truly tapped into the dark melancholic humor of the lyric like Yearwood’s did.  Credit that to her ability to bring a bit of country heartache into the melodic chorus, which soars in a way that the other recordings of “Sad Eyes” do not. – KJC


“I Would’ve Loved You Anyway”

Written by Mary Danna and Troy Verges


Country #4 | Pop #44

Grade: B+

After the singles from Real Live Woman failed to earn the radio play they deserved, Yearwood recognized that narrow-minded Program Directors were most likely to embrace her power-ballads, so she went back to that well with the lead single for her new album. “I Would’ve Loved You Anyway” is sweeping and dramatic, with an outsized chorus that gives Yearwood ample room to belt and hit some effortless high notes. The song itself is superior to some of her earlier attempts to replicate the success of “How Do I Live.” Thematically, it’s of a piece with “The Dance,” in how it considers a multitude of outcomes to the decisions we make, and Yearwood sings the refrain with a knowledge of that complexity that doesn’t change the clarity of her decision-making. – JK


Inside Out


United States:

Country #1 (1 week) | Pop #29

Track Listing:

Love Alone

I Would’ve Loved You Anyway

For a While

Seven Year Ache (with Rosanne Cash)

I Don’t Paint Myself into Corners

Harmless Heart

Inside Out (with Don Henley)

Love Let Go

Melancholy Blue

Second Chance

Love Me or Leave Me Alone

When We Were Still in Love

Later Editions Also Include:

Squeeze Me In (with Garth Brooks)

Upon its release, Yearwood noted that Inside Out was the fastest she’d recorded an album since her debut ten years earlier.

But while that first album had the tentative reservedness of a new artist in the studio for the first time, Inside Out shows a master at work, showing a new looseness in the studio that makes much of the album feel like a jam session.

“I Don’t Paint Myself into Corners” is one of her all-time great singles, as Jonathan notes below, and there are several other tracks that are in the same league as that masterpiece of a record.

“Harmless Heart” and “When We Were Still in Love” are presented simply as piano ballads, showcasing the strength of each song’s lyrics and giving Yearwood an opportunity to use the subtler shades of her voice. Along with her winning cover of “Seven Year Ache” and the wry humor of “For a While,” these four songs show Yearwood’s knack for taking literate and sophisticated material, and making it accessible to mainstream country listeners through her sheer talent as an interpretive singer.

The only slight against Inside Out is that it isn’t grounded in live instrumentation the way her work with Garth Fundis is, so some of the tracks have that dated mechanical drum sound that mars albums from the same time period by her “Holy Trinity” contemporaries Patty Loveless and Pam Tillis. It drags down “Love Alone” and “Love Let Go,” which would’ve soared with the more organic arrangements that Fundis and Yearwood created for the uptempo tracks on Real Live Woman.

Those nitpicks aside, Inside Out is easily the best of Yearwood’s three albums not produced by Garth Fundis, and compares favorably to releases like The Song Remembers When and Everybody Knows. – KJC


“Inside Out” (with Don Henley)

Written by Bryan Adams and Gretchen Peters



Grade: C-

If “I Would’ve Loved You Anyway” was an attempt to embrace her (incorrect) reputation as a ballad singer, “Inside Out” looked to recapture the magic of “Walkaway Joe” by reuniting Yearwood with Don Henley. That it didn’t work at all has nothing to do with either vocalist. “Inside Out” simply isn’t a well-written song: It has a whole lot more in common with the drippy Adult Contemporary ballads that co-writer Bryan Adams recorded a decade prior than it does with anything else in Gretchen Peters’ rich catalogue. The rhymes are hokey and juvenile, and the melodic cadence of the chorus has a sing-song quality that undercuts the notion that these are things real adults are saying to each other. – JK


“Squeeze Me In” (with Garth Brooks)

Written by Delbert McClinton and Gary Nicholson



Grade: B+

The obligatory copy-paste for all of their duets: The distinct timbres of their voices just do not sound good together, but there’s no telling them that.

That’s less of a liability on “Squeeze Me In” than on most of the other Yearwood – Brooks duets, because the song is really about two people who are just trying their damnedest to make the whole crazy thing work. It’s a fun song that actually sounds like it was fun to record, and how cool was it to hear another McClinton cut on the radio? – JK

“I Don’t Paint Myself into Corners”

Written by Trey Bruce and Rebecca Lynn Howard



Grade: A

I won’t derail this feature with a rant, but I’ll just say that, of all of the women who were attempting to make inroads in country music in the immediate, deeply misogynistic aftermath of The Chicks’ incident, Rebecca Lynn Howard deserved to be a real superstar.

Give or take “The Song Remembers When” and “The Matador,” I’d argue that “I Don’t Paint Myself Into Corners” is the finest example of Trisha Yearwood’s interpretive skill. From a purely technical perspective, it’s a beast of a song to sing, with lyrical enjambments that span multiple line breaks, a high note that’s placed at the tail end of a melodic line, and a dynamic range that requires complete control of both head and cheat voices. Yearwood aces every one of those tests, reaffirming that there are very, very few vocalists either before or after her who can do what she does. 

What makes this one of her career-best singles, though, is that it’s also a showcase for Yearwood’s emotional capacity as a stylist. It’s all about the subtle choices she makes throughout the song to emphasize the different emotional beats. She drops into her lower register and delivers the admission, “In the light of truth, who’d have thought it was me,” in a whisper that sounds tinged with both regret and shame. She lets loose with an outright wail of liberation (“But when I let you go, I set myself free”), unexpectedly at the end of a verse instead of in one of the choruses. She breaks her voice in the middle of the final word of the song– a held “anymore”– in a way that conveys that she’s letting go of all of the residual pain she’s still held onto in the aftermath of this doomed relationship, and it’s the most riveting, most perfect single moment of her entire career. 

A brilliant composition, delivered by the only singer in the genre who could ever do it full justice. Of course it missed the top 40: It would’ve laid bare the utter shamefulness of this era of country radio. – JK

A Trisha Yearwood Retrospective

Previous: Part Four: 1997-1999 | Next: Part Six: 2005-2009



  1. One of the reasons I think Trisha developed a reputation as an Albums artist is that she knew very well that the careers of the women she revered so much, especially Linda, were based as much on complete albums as the hits that came from them, if indeed not more so. This kind of goes against the Nashville grain, which is so “hit-driven” that anything else that’s not a hit on an album is, at least in their minds, mere filler. But Trisha is savvy enough to know better (IMHO).

  2. Yes! I’ve been waiting for this entry since you first started this retrospective back in 2019. This was the period in which I was first introduced to and fell in love with Trisha Yearwood. I was thirteen years old when she released Real Live Women in 2000, and I remember being absolutely captivated by the title song and its video every time it played on CMT. Since most of my music diet at that time consisted on the teen pop acts of the late nineties, RLW (the album) completely shattered my view of what an album could be. Even as a young teenager I was completely mesmerized by each song’s unique, mature perspective, and I spent so much time analyzing the brilliance with which Trisha brought new shadings (emotional and vocal) to the different tracks. (As a male choir singer I was a late bloomer and had a soprano singing voice until my high school years, and I gave myself permission to wail along to “Try Me Again” any chance I had.) The physical CD was positioned in a very prominent spot on my album shelf, and its jewel case got a little bit of paint on it when we repainted my room that year. I still have the CD in its original case with the faint hint of blue paint on it, and I’m not totally sure why this matters so much to me but it’s one of my favorite nostalgia pieces. Its follow-up was definitely a bit of a disappointment in comparison, but even Inside Out needs to be praised for introducing me to Rosanne Cash and Don Henley, which in turn brought me to Hearts in Armor and Trisha’s OG Henley collab. “Walkway Joe.” I can’t overstate how important this pair of albums is to me as a fan of both country music and Trisha Yearwood. Your write-ups here so closely mirror my own opinions, and I thank you for devoting so much time and thoughtful analysis to Trisha!

  3. I love “Where Are You Now” but feel like I have heard a different version or something. I only hear like 1 actual high note on “used to beee” for example. I also don’t see where the “Noooow” into the second chorus is all that much longer than the one into the first chorus (maybe half a second).

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