Shasha Damilola Alesh better known by his stage name Dice Ailes, is a Nigerian singer, songwriter and rapper. In July 2014, he signed a record deal with Chocolate City. He was nominated for Rookie of the Year at The Headies 2016. In 2016, TooXclusive ranked his breakthrough single "Miracle" third on its list of the "Top 10 Songs for the month of October". In 2017, tooXclusive named him as "one of the sixteen artists you need to know.

The Headies 2016 was the 11th edition of The Headies. It was held on December 22, 2016, at the Eko Convention Centre in Victoria Island, Lagos. Themed "Think, Create, Recreate", the event was hosted by Adesua Etomi and Falz. The nominees were announced by the award's organizers in November 2016. 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. Jazzman Olofin and Adewale Ayuba jointly performed the song "Raise the Roof". Aramide performed her song "Funmi Lowo" with assistance from Ras Kimono. The ceremony also featured additional performances from Falz, 2Baba, Seyi Shay and Flavour. Olamide received eight nominations and won a total of four, including Best Rap Single for his single "Eyan Mayweather". Mr Eazi won the Next Rated category and was awarded a SUV at a later date. Mayorkun toppled Dice Ailes and Koker for the Rookie of the Year award. Laolu Akins was honored with the Hall of Fame award, while Flavour received the Special Recognition award.