Two of Hilltop Hoods' founders first met in early 1990s when MC Suffa (aka Matthew David Lambert) and Pressure (Daniel Howe Smith) attended Blackwood High School in Eden Hills – a suburb of Adelaide.

The band's influences include American hip hop artists: Notorious B.I.G., KRS-One, Gang Starr, Wu-Tang Clan and Public Enemy.

[5] Fifth track, "Mankind Must Suffa" also features a guest verse from Quromystix (aka Quro, Andrew Michael Bradley) – a member of Finger Lickin' Good and later the Fuglemen.

[8] The album was released independently but with financial assistance from Arts SA – the band were inspired, in 2005, to set up their own Hilltop Hoods Initiative, to help local artists.

Hilltop Hoods founded the Certified Wise Crew – a hip-hop collaborative – with local groups Terra Firma, Cross Bred Mongrels and After Hours.

Hilltop Hoods' chart and commercial success was a turning point in the Australian Hip Hop scene because it demonstrated widespread support for the genre that reached beyond an underground fan base.

[20] The track, "The Blue Blooded", is a collaboration with Australian MCs: Funkoars, Hau from Koolism, Mortar, Vents, Drapht, Muph & Plutonic, Pegz and Robby Balboa.

[19] On 27 April of the same year, Hilltop Hoods performed at the Bass in the Grass music festival in Darwin alongside fellow hip hop group, The Herd.

That year the group performed at the Southbound Festival (WA), The Great Escape at Newington Armory over Easter, and embarked on a UK tour with a Sydney-based string quartet.

In November 2008 Pressure announced on Triple J's breakfast program that the next studio album, State of the Art, would be recorded with session musicians: "We realised with this one after doing Restrung and having an orchestra that we were a bit less limited.

[25] The album was released on 12 June, with the lead single, "Chase That Feeling", issued as a digital download on 8 May,[26] and featured a return guest appearance by a quartet from the Adelaide Symphony Orchestra.

[39] In August 2012, Triple J uploaded video footage of the group's tribute to Beastie Boys' member, Adam "MCA" Yauch, who died in May 2012.

It featured numerous Australian hip-hop artists, including Drapht, Urthboy, Def Wish Cast, Dazastah, Layla, Maya Jupiter and Hunter.

[44] In April 2013, the Hilltop Hoods stated that the development of Walking Under Stars was "well underway", with the trio calling the album Drinking from the Sun "part two"—the latter received a double platinum sales certification in the same month.

Additionally, American clothing company Zoo York announced a partnership with the Hilltop Hoods in April 2013, in preparation for the brand's 20th-anniversary celebrations in 2014.

Lambert explained in media interviews during the week prior to the album's release that the song was recorded at the Red Bull Studios in both London, UK and New York City, US, while the lyrical content is about the partners of the band members and the difficulties of being in a relationship with touring musicians.

[48][49] During the band's performance at the 2014 Splendour in the Grass festival, held from 25 to 27 July in Byron Bay, Australia,[50] Lambert exclaimed to the audience prior to the song "Speaking in Tongues", from the Drinking from the Sun album:

[51] The band announced the release date for Walking Under Stars as 8 August 2014 in mid-July and, while the album is a Golden Era Records recording, Universal Music Australia acquired the exclusive licensing rights for the domestic market—Universal will also use the license to distribute the album in Canada, Austria, Germany, Switzerland, the United Kingdom, New Zealand and Benelux, while Golden Era continues its partnership with Fontana for the US release.

As of 16 August 2014, the Hilltop Hoods have garnered a total of six weeks at the top of the ARIA charts from four number-one albums, three of which are Golden Era Records releases.

[54] During the promotion for a national Australian tour in late August 2014, the band revealed that a secret release will "manifest itself" in 2015 and will be the culmination of a multi-album creative project that began with Drinking From The Sun.

[57] The music video for the "Cosby Sweater" single was released on the Hilltop Hoods YouTube channel while the group was engaged in the third stage of their 2014 world tour in North America.

On 8 December 2012, the Hilltop Hoods were one of two headlines acts (the other was American band, Blondie) for the 2012 "Global Edition" of the popular Australian music, film, comedy and arts festival, Homebake.

[69][70] The band announced an August–September 2014 North American tour in June 2014—including dates in Vancouver and Toronto, Canada, and San Francisco, US—with Minnesota, US, artist Sims, from Doomtree.

In February 2019, the group supported Eminem's concert tour around Australia and New Zealand, performing to audiences in venues such as ANZ Stadium in Sydney and the MCG in Melbourne.

[73] Hilltop Hoods undertook a national tour in late 2022, commencing in Brisbane on 27 August, with performances in Sydney, Melbourne, Perth and concluding in Adelaide.

A photograph of Suffa holding the award in the presence of the band was posted on the Hilltop Hoods' Instagram profile, accompanied by the following comment: "A memory I'll take to the grave.

Valued at A$10,000 (originally $3000), the Hilltop Hoods initiative helped young and emerging South Australian hip-hop artists to manufacture and distribute a CD.

This label wasn't established to release throw-back records; instead we hope to make music that throws you back to the way you felt during the golden era of Hip Hop.

[125]The label is based in Stirling, South Australia, and, as of December 2012, its roster consists of the Hilltop Hoods, Briggs, Funkoars, Vents, Adfu, K21,[125] and most recently, Shadow.

In January 2012, Fontana, an independent marketing, sales and distribution company under the Universal Music Group umbrella, signed an exclusive agreement with Golden Era Records for the American release of Drinking From The Sun, as well as back catalogue titles.