[2] They left their home in the Bronx at age 17, spending time crossing North America, hopping freight trains.

[2] Around 2007, Segarra became a part of the Dead Man Street Orchestra, a hobo band that was documented in a photo essay by Time magazine in 2007.

[3] Segarra traveled with the group for two years, releasing two independent albums and embarking on freight train tours across the country.

In February 2011, Hurray for the Riff Raff were featured in an article in UK newspaper The Times based around the HBO TV series Treme, with their track "Daniella" having been included in the show's selection of New Orleans' essential songs.

[4] On March 21, 2011, Hurray for the Riff Raff released their self-titled CD on Loose Music in Europe, composed of Segarra's favorite songs from the band's two previous records.

The Wall Street Journal describes Segarra's singing thus: "She has a subtle, expressive voice that she wraps around songs that draw on the sounds and styles of the American South, and her lyrics often take unconventional tack on traditional subjects.

[14] In late 2018, Segarra joined organizers of the Newport Folk Festival to travel to Puerto Rico and deliver instruments to various public schools.

[21] The Associated Press named the album to its list of the best work from 2024, calling it a "beautiful portrayal of the U.S." and noting that Segarra pulled from their background as a hitchhiker, train hopper and outsider artist to document adventures "that can only happen far from home.