Various media personalities in Nigeria have hosted the ceremony, including Darey Art Alade, D'banj, Dakore Egbuson, Banky W., Rita Dominic, M.I, Tiwa Savage and Dr SID.

It represents the "image and the shout of a young, vibrant individual whose talent can challenge that of renowned local and international artistes combined, but who has almost lost confidence in his abilities in the face of discouraging circumstances presented by the peculiar Nigerian environment."

[4] 2006: The 1st edition of the Hip Hop World Awards was held on 10 March 2006, at the Shell Hall of the MUSON Centre in Onikan, Lagos.

[5] DJ Jimmy Jatt, Keke Ogungbe and Dayo 'D1' Adeneye were joint winners of the Hall of Fame award.

[7] 2008: The 3rd edition of the Hip Hop World Awards was hosted by comedian Basketmouth and Nollywood actress Dakore Egbuson.

[12][13] 2010: The 5th edition of the Hip Hop World Awards took place on 16 May 2009, at the Eko Hotel and Suites in Victoria Island, Lagos.

[15] 2011: The 6th edition of the Hip Hop World Awards was held on 22 October 2011, at the Eko Hotel and Suites in Victoria Island, Lagos.

Tiwa Savage and Wande Coal won the Best Male and Female Vocal Performance categories, respectively.

The Headies celebrated the reunion of prominent Nigerian musicians from the 80s and 90s, including Onyeka Onwenu, Oris Wiliki, Mike Okori, Baba Fryo, Shina Peters, Fatai Rolling Dollar and Daddy Showkey.

Veteran Fuji artist Wasiu Ayinde Marshall was inducted into the Headies Hall of Fame.

[28] 2 Face Idibia, Banky W., Waje, Nikki Laoye, Mode 9, Dr SID and Kcee all went home with a plaque.

[29] 2014: The 9th edition of The Headies took place on 14 December 2014, at the Eko Hotel and Suites in Victoria Island, Lagos.

Don Jazzy won the Producer of the Year plaque, while Sir Victor Uwaifo got the Hall of Fame recognition.

It was previously scheduled to hold on 30 December 2015 but the organizers of the event postponed it to 1 January 2016 without citing any reason.

[44] Tekno was nominated for the Next Rated award, but ended up being disqualified due to his refusal to honour the category and support the campaign.

[50] After shortlisting thousands of entries submitted during the eligibility period, the organizers of the ceremony announced the nominees in April 2018.

The ceremony featured performances from a number of artists, including Falz, Mr Real, Simi, and the Danfo Drivers.

Mayorkun won the Next Rated award, beating Dice Ailes, Maleek Berry and Johnny Drille.

[52] 2019: The 13th edition of The Headies was held on 19 October 2019, at the Eko Convention Centre in Victoria Island, Lagos.

Themed "Power of a Dream", the ceremony was hosted by Nigerian rapper Reminisce and actress/media personality Nancy Isime.

[53][54] After shortlisting thousands of entries submitted between January 2018 and June 2019, the organizers of the ceremony announced the nominees on 1 October 2019.

The ceremony featured performances from a number of artists, including Styl-Plus, Sunny Neji, Duncan Mighty, Teni and Victor AD.

Rema won the Next Rated award, beating Fireboy DML, Joeboy, Lyta, Victor AD and Zlatan Ibile.

[58] 2020: The 14th edition of The Headies[59] was held on 21 February 2021, at the La Campagne Tropicana Beach Resort in Ibeju-Lekki.

Event organizers announced that TV personality and actress Nancy Isime and comedian Bovi were the hosts.

2023: The 16th Headies Awards took place on Sunday, September 3, 2023, at the Cobb Energy Performing Arts Center in Atlanta, Georgia.