Prettymess was established in 2003 by John Baxter and Paul Inglis, both of whom were formerly members of the Melbourne band Alcotomic. After Alcotomic disbanded in 2001, Baxter and Inglis spent much of 2002 creating new music, collaborating with notable artists such as Andy Strachan from The Living End, Michael Snowball from Groundswell, and Danny McDonald from P76.

The music management company Ridgeway/Dacy took notice of their demo for "Rescue Me" and offered them a spot on their roster, which also included Taxiride and The Androids. Shortly thereafter, guitarist Ryan Temby and drummer Paul Cengia joined, leading the band to abandon their temporary name, Polarised, in favor of Prettymess. They performed their first showcase gig on January 28 at the Evelyn Hotel in Fitzroy.

Initially facing challenges related to direction and financial support, the band became disillusioned with their management team and amicably parted ways in mid-2003. However, adopting a DIY approach, they signed a two-album deal with the Australian indie label Shock Records after their song "Tripping" caught the attention of the label. They soon partnered with national booking agent Premier Artists.

In mid-2003, "Leaving Look," which would later open their debut album, was included in the Lost Weekend compilation released by Laughing Outlaw Records in Australia and Zip Records in the United States. This compilation showcased some of the best emerging independent bands from Australia that year. Later that same year, their punk-influenced track "Inspiration" was featured on the Australian Surf Life TV series, significantly raising the band's profile.

On March 5, 2004, Prettymess released their debut EP, Surface Glow, which was mixed by Craig Lewis at Kaleidoscope Music in Adelaide and included the critically acclaimed single "Tripping." The EP entered the AIR top 20 and maintained its position for several weeks while the band toured nationally alongside The Fauves, Epicure, and Killing Heidi. The Australian Financial Review described it as “an impressive EP by the rising Melbourne band,” highlighting its blend of melody with hard-hitting guitars.

In September 2004, after receiving a VicArts artist development grant, the band returned to the studio to work with renowned producer/mixer Shane O’Mara on their debut album, Greyscale Broadcast. Following two additional tours through Tasmania and Victoria, the 11-track album was released on February 21, 2005, with "Rescue Me" as the lead single. JB HIFI Magazine characterized it as “superior pop rock, catchy and classic.”

The music video for "Rescue Me" received rotation on Channel V and Rage, while Nova 100 and Triple M added the song to their high rotation playlists. The band toured extensively with acts such as the Church, Thirsty Merc, and MotorAce. A live review in Seed Magazine noted that Prettymess outperformed other acts at a show in Prahran, stating: “If you love your dancy Rock'n'Roll; Prettymess, just check 'em out.”

The latter part of 2005 was marked by a series of sold-out shows, including performances with the US band Switchfoot at the Forum Theatre and HiFi Bar in Melbourne. After a headline tour of Tasmania in April, the band concluded the year with their final live performance, supporting MotorAce in front of a full house of over 900 people at the HiFi Bar on December 23, 2005.

Although the band began rehearsing again in early 2006, it wasn't until May 2008 that they reformed to record five new songs at Birdland Studios in Prahran with MotorAce drummer Damian Costin. Ultimately, the band decided not to continue, but three tracks from these sessions—"Evolve," "Slow Moving Traffic," and "Silver Sun"—were included on Five Mile Sniper's EP and album.