Fly My Pretties kicked off in 2004 with a five-night residency of original folk and rock songs, performed at Bats Theatre in Wellington. Recorded live, later that year they turned the best of the recordings into an album Live At Bats.

Real Groove hailed it thus: “... the all star line up straddles dub, soul, funk, rock, country and pop seamlessly, bound by relentless and infectious heart.”

Live at Bats achieved platinum sales status in New Zealand, was released in the UK, received six nominations at the 2005 B-Net New Zealand Music Awards and walked away with the award for Best Pop Release.

In 2006 they returned with a second series of concerts and an associated live album and DVD package called The Return, achieving platinum record sales. They toured The Return to sold out audiences around New Zealand. The next year The Return won them Best Aotearoa Roots album at the New Zealand Music Awards.

Two years later in 2009 they performed a third show cycle Fly My Pretties – A Story. They again toured it nationally and released it as a live album/DVD package. The album reached No.1 on the Top 40 Album Charts in New Zealand. It was also nominated for Best Aotearoa Roots album at the 2010 New Zealand Music Awards. For Fly My Pretties – A Story, the group was joined on stage by Weir's father Dick Weir to narrate the story.

In 2011 they performed another cycle of shows around the country, again recording and releasing them as a live album/DVD package titled Fly My Pretties IV. As part of this, they travelled to Australia for their first international date, playing a sold out show in Melbourne.

Fly My Pretties has also performed spot shows on the summer festival circuit and playing vineyard dates.