Hello friends, and welcome to “The Annotated Road Taken,” Episode 6. As always, what follows is audiovisual context for our in-depth conversation about touring and the events that make up a career. This week, we talk with the incredible Michelle Branch.

Michelle’s career started at age 16, just two years removed from strumming her first guitar chord, and she quickly reached heights that few musicians ever see: a double-platinum debut album, multiple hit singles, a cameo in the Rob Schneider vehicle The Hot Chick. But for every MTV Moonman handed off by ’NSync, there was the grind of a solo acoustic show in Paducah, Kentucky, or an awkward Luxembourgian television show to get through, with all the work contributing to an incredible amount of success.

As Michelle’s career and life progressed, however, the balance between peaks and valleys became harder to maintain. Despite repeated success in both the pop and country worlds, various gatekeepers refused to let Michelle exert full agency over her career, and what could have been many productive years instead became frustrating ones. Through feast and famine, though, she has always written and worked hard, growing as a performer and giving her charming best for her loyal audience.

For me, that vague notion of “Hmmm, maybe music is something I could try to do?” was kind of illuminated by watching Michelle, only one year older than me, write great songs and perform them so well in every platform she was given. To be able to sit with her and talk through her experiences—some joyful, some not—as something of a peer was a true pleasure, and I can’t thank her enough for her time. In a very thorough conversation, we discuss why she liked guitar techs more than the boys in the band, how she drew inspiration from the Dixie Chicks as touring mothers, and having to fire her father at the age of 18.

Let’s get into it!

12:25 “My mom was a manager of a Mexican restaurant, and so I’d play in the bar …”

After receiving her first guitar at age 14, a precocious Michelle began writing songs and performing them live almost immediately. Some of her earliest gigs in her hometown of Sedona, Arizona, were in the restaurant where her mother worked at the time, which appears to be the Javelina Cantina. Love a place that has supposedly world-class margaritas and also allowed a young Michelle to “make bank” on tips.

17:35 “I knew C, G, F, A minor, E minor, and D …”

If you have an innate musical skill set like Michelle, these are the guitar chords you need to start a career.

21:12 “I could barely hear myself over screaming teenage girls …”

Directly before signing a record deal and experiencing her own rush of success, Michelle got a taste of what was to come when she opened a few shows for Hanson in the summer of 2000. Hanson was touring for their second major-label album, This Time Around, and their shows at the time seem to have melted even the coldest, most critical hearts; hell, even John Popper came down to sit in! The Hanson–Michelle Branch connection proved lasting, as Michelle sang some guest vocals (complete with an excellent over-the-headphones hat) on their song “Deeper” a few years later.

24:08 “Oh my God, I’m horrified that’s online …”

Don’t be horrified, Michelle, it’s very charming! This is Michelle’s first “radio promo” show, which are usually performances in a setting of the station’s choosing and a way for an artist to say “thank you” for their support of a particular song or album. In this case, Michelle is performing directly after a tractor race in Paducah, Kentucky. Despite a memorably bad travel day, she still displays a confidence and poise well beyond her then 18 years. I personally agree with the enthusiastic emcee here when he says, “You gotta give it up for Miche-yelle Branch!!!”

26:07 “My label flew the whole band out to basically lip-synch …”

Michelle was not happy with this U.K. promo gig, as the powers that be allowed only her lead vocals to be performed live. At the time, lip-synching (even with its attendant pitfalls) was generally pushed by higher-ups to prevent potential mistakes or bad live sound from marring a performance with wide-reaching exposure. Today, however, there’s so much digital information in live performances that the idea of “backing tracks” or altering an arrangement for television is not really the issue or debate it was in 2002. Seems like Michelle and her band made the best of it at the time (“This is funny,” she quips at the outset). Special props to the drummer at 00:17 for really selling it!

45:03 “Do we like each other? Do we not like each other? Everyone keeps confusing us ...”

Here Michelle is referencing her alleged rivalry with contemporaneous female artists Vanessa Carlton and Avril Lavigne. This reductive moment in time is best summed up by this VH1 news item about artists who “focus more on their songs than their abs.” While Michelle, Vanessa, and Avril were all young women who played instruments and wrote songs, they were all very different and didn’t need to compete with one another (despite some epic fictions to the contrary). According to Michelle, there was never much to it but, thankfully, we will always have those early-’00s memories.

52:46 “It felt like a whole album cycle in and of itself …”

In between Michelle’s first and second albums, she landed another incredibly huge hit with her Santana collaboration “The Game of Love.” As befits the single that followed up Santana’s Supernatural success and charted in over 20 countries, there were quite a few promo performances to get through.

54:38 “It was Macy Gray, Tina Turner, and Gregg threw my name in the mix …”

As part of the process of creating “The Game of Love,” Michelle, Tina Turner, and Macy Gray were all brought into the studio by producer Gregg Alexander to give the song a shot. Alexander had found success years earlier as the driving force behind the New Radicals and their hit song “You Get What You Give,” which Michelle and her band occasionally covered. Having never heard “The Game of Love” before her day in the studio, Michelle used Alexander’s demo of the song as a guide and proceeded to perform so well that she made the final cut and landed another pre-age 20 smash hit.

59:15 “I think the weirdest thing was Beyoncé was doing it with me …”

This marks our first Beyoncé story on The Road Taken, a truly momentous occasion! One of the many “The Game of Love” promo performances was the pregame show for Super Bowl XXXVII (the Gruden Bowl) and featured a newly solo Miss Knowles also guesting with Santana. What vibes must have been pulsing through their shared dressing room that afternoon, as a minimally rehearsed Michelle and Beyoncé prepared to go live before the biggest audience in American television? Michelle’s favorite moment, the impromptu do-si-do, comes at 9:38 in this video. Michelle, if you’re reading this, the GIF is below.

1:02:37 “For the years I went ‘missing’ I had a country duo called the Wreckers …”

Indeed, after some issues with her label, Michelle turned to a more country sound and formed the Wreckers with Jessica Harp. They hit no. 1 on the Hot Country Songs chart with their first single “Leave the Pieces” and had a good run of touring for a few years (and even reunited in 2017 during Michelle’s show in Nashville that year).

1:11:18 “It did not go over well …”

Michelle is referencing a tour opening for the Goo Goo Dolls in 2011, in which she didn’t bring a full band and instead relied on loops and tracks to fill out her live sound. From the evidence I can find, it doesn’t seem like it went down as poorly as she remembered it. She even had a nice way of explaining her lack of a drummer (“He’s in prison”). Looks like the Goos were also in fine form that summer.

1:14:04 “Patrick has such an incredible business mind …”

I agree! Patrick Carney graced The Road Taken with some of his renowned business acumen on our debut episode (recorded just minutes after this conversation with Michelle finished).

1:20:03 “We played the closing show at Webster Hall …”

After finally being released from record-label purgatory, Michelle released Hopeless Romantic in April 2017. One of her favorite shows from this run was one of the last shows at Webster Hall in New York City before it closed for extensive remodeling. The title track sounds great, as does the song “City” and the meaningful stage banter preceding it. Honorable mention goes to the 9:30 Club, a legendary venue in Washington, D.C, for the particularly raucous singalongs.

1:22:24 “There’s a lot of stuff I wish I said yes to but I was just too scared …”

While doing promo for Hopeless Romantic, Teen Vogue asked current-day Michelle to give advice to her 18-year-old self. Crazy to think that Michelle’s 18-year-old self was already an incredibly successful musician and business woman and yet there were still many lessons to be learned!