Alynda Segarra’s Hurray for the Riff Raff/Photo: Denny

Singers and artists often spin tales of their early lives and careers in the hope of building a deliberate myth. Some claim criminal backgrounds and brushes with the law, while others try to camouflage an upper-class suburban upbringing. Even Bob Dylan tells stories about traveling with carnivals and circuses as a youth.

Yet Hurray for the Riff Raff’s Alynda Segarra has walked the legendary walk of American folk mythology. Born in the Bronx to a Puerto Rican family, they ran away from home at seventeen and spent much of the next decade hitchhiking, busking on the streets of New Orleans and riding the rails like Woody Guthrie. (Segarra is non-binary and uses the pronouns they/them.) Their songwriting has won praise within the music literati. Their “The Body Electric” was named song of the year in 2014 by Americana Songwriter, and their 2024 album “The Past Is Still Alive” was nominated for album of the year at the 2024 Americana Music Awards in Nashville. Segarra and Hooray For the Riff Raff recently settled in Chicago and have released a live album,“Live Forever.” The album contains songs from the Riff Raff’s previous albums, as Segarra adds live energy to the poetic messages in songs like “Alibi,” “Colossus of Roads” and “Precious Cargo.”

But this is no surprise, as Segarra has spent over two decades performing on the streets of New Orleans, on trains, in houses, shelters and, more recently, at the Newport Folk Festival and The Kennedy Center for the Performing Arts.

It all started in the Bronx, where Segarra attended punk shows at ABC No Rio, the artist’s community and poetry center formed in 1980 in an abandoned building on Manhattan’s Lower East Side. But at seventeen, they became restless.

“I knew I was doing bad in school and I ended up running away,” Segarra tells PBS NewsHour. “I traveled by hitching with friends and riding freight trains because Woody Guthrie rode freight trains. I knew it could be dangerous, but I was always with other people. We were just a group of kids trying to survive on the outskirts of society.”

Alynda Segarra’s Hurray for the Riff Raff with “Live Forever”/Photo: Alexa Viscius

Segarra ended up in a place where many cultural wanderers and misfits find an oasis: New Orleans. But the New Orleans that Segarra traveled to was not the New Orleans of the Jazz and Heritage Festival, filled with upscale visitors staying at VRBOs and “finding their NOLA soul.” It was the New Orleans of Katrina. A desolate, dystopian world filled with houses that had so much mold and mildew it was as if someone had taken a winter’s worth of Chicago snow, dyed it black and spattered it over the walls. Four months after Katrina, Segarra joined The Dead Man Street Orchestra. The group became known throughout the underground culture of New Orleans and beyond for their mix of blues, jazz, ragtime and traditional hymns as well as their street presence and “hobo” existence, which included playing on the street, in homes, buses and even in laundromats.

A self-described poet with inspiration from artists including Guthrie, Walt Whitman and the Nuyorican poets of the Bronx, Segarra had little or no musical experience. They started by playing washboard, then a banjo. The group played what we now call Americana—blues, early jazz and traditional songs like “Crow Jane” and “You Are My Sunshine.”

Finding little money in New Orleans, the band and Segarra returned to riding the rails on what they called “boxcar tours.” In February 2007 the band’s rail riding was featured in “The Ballad of the Hobo,” a 2007 photo essay by James Heil in Time.

With a sponge-like mind for anything cultural, Segarra absorbed everything from Bessie Smith to Patti Smith. They began playing guitar, writing songs and formed Hooray For The Riff Raff, releasing the albums “It Don’t Mean I Don’t Love You,” and “Young Blood Blues.” Their years of paying dues on the Crescent City’s streets also earned the Riff Raff song “Daniella” a spot on the soundtrack of “Treme,” HBO’s New Orleans-based series.

In the next decade, Segarra and the Riff Raff released three albums, “My Dearest Darkest Neighbor,” “Small Town Heroes” and “Navigator.” The influences on these albums ranged from Leadbelly to John Lennon to Billie Holiday, Hank Williams and future collaborators Lucinda Williams and Norah Jones.

As their reputation grew in the independent, folk and alt-rock circles, Segarra lent their name and music to social and political issues, many of which are a direct reflection of their life experiences, including being a strong advocate for LGBTQ+ causes. After describing to Rolling Stone an abortion they received at the age of nineteen, they started championing women’s rights. Segarra uses their pen, guitar and spirit to write and play songs warning of the dangers of global warming too, which they saw firsthand post-Katrina.

The newest chapter in Segarra’s book is a move to Chicago.

This may be a result of Riff Raff guitarist, tour manager and sound engineer Johnny Wilson being a Chicagoan. But Segarra’s train-riding wanderlust may have also played a role. Like many artists, the change seemed to fuel creativity. This spring, the group released “Live Forever,” which was recorded last fall at the Old Town School of Folk Music. With fourteen songs, the album demonstrates the mastery Segarra and Riff Raff have gained playing Americana in America for almost twenty years. It begins with “Alibi,” which rolls along like a car crossing the plains and heading into the Badlands. “Dynamo” has a country sound, while “Buffalo” is more of a slow folk ballad, and “Precious Cargo” with a statement against ICE, has a hip-hop feel. “Pyramid” has a bouncy, almost pop groove, with Parker Grogan adding a blues touch with slide guitar.

The album is another triumph by Hurray For the Riff Raff, a band whose members often change, but has always been anchored by the words and music of Segarra, who explains the birth name of the group. “The people who have gotten me through my life are the weirdos and the poets, the rebellious women and the activists,” Segarra says. “They were considered the riff raff by the people in power, but they are the ones who made history.”

Hooray for the Riff Raff  play July 10 at FitzGeralds, before embarking on an East Coast tour, which includes dates with Rhiannon Giddens, Mary Chapin Carpenter and Mavis Staples.

Published in the print edition of the June 2026 issue, with the headline “The Rail-Riding Folk Hero: Alynda Segarra Lands In Chicago With A Live Album.”