Little Jill & The Frog began their career as part of the West Australian busking scene, and had their first live performance in Perth’s Murray Street Mall on 14 February 2000. Throughout the year they continued to perform outside various retail establishments and built a solid name for themselves alongside other local busking outfits such as The String, and Jam Rocket 66. 

In April, the band’s mainstream breakthrough came when they won a national competition called Street Talent, performing ‘Lets Shake Hands’. The competition was conducted by the Australian Broadcasting Corporation (ABC) alternative radio station Triple J. As part of the prize, Triple J recorded and distributed 1,000 copies of the song.

The popularity of ‘Let’s Shake Hands’ led to a bidding war between major labels which resulted in Little Jill & The Frog signing a three-album contract with Paedamonte Records on 14 April 2001.

In June, their Triple J recording was re-recroded as a four-track extended play. It spent two weeks at number-one on the ARIA Singles Chart. In September, the follow up single ‘Oranges and Blue’ was released and a quirky video was made for the US market. It became the most played song on American college radio that year.

Their debut album, Is Trees Made of Leaves, was recorded in a single eight-hour session by Francis Cohen, and was released on 1 October 2001. Rock critic Mickey Farlane reviewed the 12 tracks as “brimming with positivity, surrealism, illusion and honesty, but above all, hard-nosed banjo.”

On 24 March 2002, Little Jill & The Frog kicked off their Australian tour by playing a 40-minute set for a group of 120 kids at The St. Vincent’s Orphanage for Girls, in South Melbourne. The tour continued throughout Australia with concerts in small halls, markets, and school playgrounds, as well as frequent “secret shows” publicised by posts on The Banana Room, an online fan message-board. 

Secret gigs on this tour included performances at a bowling alley in Geelong, a Wodonga bus station, the YMCA in downtown Kalgoorlie, and a famous three hour show at the Salvation Army homeless shelter in Lismore. Video clips from several of the shows have been posted on YouTube.

After the tour, The Frog immediately began working on songs for the band’s next album at his pond’s home studio. He experimented with different techniques, sometimes trading in his electric banjo for a Rickenbacker. 

Little Jill & The Frog’s second album, Disco At The Birdbath, was released on 11 June 2004. Produced by The Frog and engineered by Slim Jim Diamonds at the legendary Blackbird Studio in Nashville, the album was dedicated to the seminal Mississippi Delta blues musician Pinetop Perkins—an artist who greatly influenced the band. 

Disco At The Birdbath contains an a cappella version, as performed by Frog, of the traditional American gospel song ‘The Wicked Shall Cease from Troubling’, and a cover of Mental As Anything’s ‘Spirit Got Lost’, sung by Little Jill. The first single ‘Sharing Watermelon’, with its extravagant banjo loop, became their signature song.

The album drew modest attention from a large variety of media outlets worldwide, and went gold instantly all throughout South and Central America, where interest in band had suddenly soared.

Looking back on the album, during in a 2015 interview with Guitar Player, The Frog said, “I don’t think we could ever top Birdbath. It’s the most raw, the most powerful, and the most mutual sounding record we could hope to make.”

Little Jill & The Frog performed at the Soundwave Sydney concert in March 2005, and followed with their first international tour, heading first to Europe, then Asia, and finally Central and South America, where Disco At The Birdbath was continuing to chart highly. 

Upon landing at the Santa Rosa de Lima Airport, in El Salvador, an uproarious crowd estimated at 3,000 greeted the duo in heavy rain, along with numerous journalists and photographers. Little Jill & The Frog took time to sign autographs and pose for pictures with fans and members of the National Guard.

While in Colombia, Little Jill & The Frog made a cameo appearance in famed movie director Francisco Norden’s prison epic El Trato. During the films opening wedding scenes they portray the Medellin Casino house band. A Spanish version of ‘Sharing Watermelon’, with extended lyrics was recorded specifically for the film.

The band also appeared as themselves in the Peruvian animated series Los Trio Alpacas, in the episode “Donni Robó la Dona”. In the same year, The Frog was one of three musicians featured in the documentary Pluckin’ Crazy. A film in which he, Ricky Scaggs, and Eric Weissberg come together to discuss the banjo and each artist’s different playing methods.

In order to complete the band’s vision for their third album, Dressing up like Fences, several other musicians contributed to the recording. Van Dyke Parks, Paul Muir (from Muir and Scratchy) and Rob Hirst (from Midnight Oil) all collaborated with the band. During the recording of Dressing up like Fences, and in all the press that followed, The Frog began to refer to himself as an artist, rather than simply being a “musician”. 

The single, ‘Champagne Under Chandeliers’, was released in January 2008 to coincide with the band’s appearance on the Big Day Out tour. In March, Dressing up like Fences was issued and topped the ARIA Albums Chart – it went on to spend 43 weeks in the Top 50.

On the ensuing tour, the duo’s performance in their home state at the Perth’s Quarry Amphitheatre, on 19 April 2008, was recorded and released as the double CD Live Carpet Jam. At the tour’s completion June 2009, the group announced an indefinite hiatus in order for Little Jill to finish high school.

Over the following year, The Frog collaborated with composer and trumpeter Snuffy Watkins. The album that resulted, Mudtide, integrated jazz, rock, ethnic and classical music into the recordings. On all of the tracks, The Frog’s trademark picking banjo style is overtaken by a twelve string electric approach.

Little Jill & Frog appeared live for the first time in eighteen months at the Falls Festival on New Year’s Eve 2010, where they performed an alternate version of ‘Mum made Biscuits’. This proved to be their final live performance as a duo.

On 2 February 2011, it was announced that the two had officially ceased recording and performing music as Little Jill & Frog. The announcement specifically denied any artistic differences or high school issues, but cited “mostly to preserve an beautiful legacy.”

The popularity and critical success of the duo opened up opportunities for The Frog to collaborate with his choice of other musicians. He continues to join other artists on their recordings, as well as them to perform on his projects. He has also worked as a producer for various acts, often through his label, Swamp Land Records.

During its brief career, the band had a notable impact on music in the Spanish-speaking world. In 2013, a Little Jill & The Frog tribute album featuring performances by Buenos Aires banjo bands such as Todos Tus Muertos, Café Tacuba, and Tijuana Overdrive. Argentina’s Los Fabulosos Cadillacs covered ‘Hats for Sunshine’ and ‘Champagne Under Chandeliers’, and also invited The Frog to sing on their 2014 album Cadenas De Locos.