Originally from Auckland, Smith was raised around blues, jazz and soul music, and at age 16 won Best Jazz Vocalist at the National Jazz Festival of New Zealand. Next she recorded a single with her stepfather, respected Celtic musician Steve McDonald. This led to her recording an album of Celtic music with him. Light From A Distant Shore was released internationally, after which Smith toured America with McDonald as an opening act. As a result she was given the opportunity to record an album of her own music in Boulder, Colorado. Due to creative differences with the label she was working with at the time, the album was never released.

At age 19, Smith relocated to Wellington, where she lived for the next half decade before returning to Auckland. While in Wellington Smith recorded and performed with Trinity Roots, Fat Freddy's Drop, Recloose and The Illphonics. During this time she independently recorded and released her self-titled debut EP.

'Bathe In The River' peaked at No.2 on the New Zealand Top 40 Singles Chart and eventually sold platinum in New Zealand.

In 2005 Smith took part in the second edition of Barnaby Weir and Mikee Tucker's (Loop Recordings) Fly My Pretties CD/DVD and live performance series. In 2006 she took part in the Bacardi B-Live OE: Brazil project, where she travelled to Brazil and recorded with The Zimbo Trio and Apollo Nove, before returning home to take part in a series of shows across New Zealand. The same year she recorded hit single 'Bathe In The River' with Don McGlashan, releasing it under the moniker The Mt Raskil Preservation Society. 'Bathe In The River' peaked at No.2 on the New Zealand Top 40 Singles Chart and eventually sold platinum in New Zealand.

In 2007 Smith released her album Long Player through her own label Soundsmith Records and EMI. Long Player was co-produced by Jeremy Toy. That year she also signed a multi-album deal with US-based Blue Note Label Group imprint Manhattan Records. Long Player peaked at No.1 on the New Zealand Top 40 Album Chart and sold double platinum in New Zealand. Next she travelled to Philadelphia to record new material with American producer James Poyser, soon releasing a deluxe edition of Long Player with several new songs.

Long Player peaked at No.1 on the New Zealand Top 40 Album Chart and sold double platinum in New Zealand.

In 2009 Smith's deal with Manhattan Records collapsed and she had to use her profits from Long Player to buy herself out of the deal.

In 2010 she released a new album Humor And The Misfortune Of Others, again via Soundsmith Records and EMI. Co-produced by Riki Gooch, Humor And The Misfortune Of Others was eventually certified gold in sales in New Zealand.

In 2011 she started a new project called Band of Brothers, which sees her collaborating on full albums with different musicians, beatmakers and producers. That year she released Vol.1 in collaboration with Mara TK, again via Soundsmith Records and EMI.

In 2012 she formed a trio with Boh Runga and Anika Moa named Anika Boh & Hollie. They released an album titled Peace Of Mind in 2013 via Sony Music New Zealand.

Outside of her collaborations with Trinity Roots, Fat Freddy's Drop, Recloose and The Illphonics, Smith has also recorded feature vocals for the likes of Solaa, Grooveman Spot (Japan), Homebrew and Concord Dawn.

On the live front, Smith has opened for Coldplay, Simply Red and Bob Dylan. She has also performed at Womad NZ and outside of performing extensively around New Zealand, toured through Australia, Europe, the UK, Asia and America.

While performing, Smith alternates between playing with a guitarist or performing with a full band. During her career she has been backed by the likes of Darren Mathieson (drums), Crete Haami-Jones (bass), Lisa Tomlins (backing vocals), Ria Hall (backing vocals), Bella Kalolo (backing vocals) and Tyson Smith (guitar) amongst others.

Over the years Smith has amassed a collection of music awards for Best Arrangement (Tauranga Jazz Festival, 1996), Best Vocalist (Tauranga Jazz Festival, 1996), Best Female Artist (NZ Music Awards, 2007), Breakthrough Act Of The Year (NZ Music Awards, 2007), Best Aotearoa Roots Album (NZ Music Awards, 2007) and Best Producer (NZ Music Awards, 2007). She has also been nominated for several other New Zealand Music Awards over the years.

Now based in Mount Manganui, Smith continues to record and perform to this day, often pulling large crowds at shows around New Zealand.