Whilst growing up, Wainaina was influenced musically by international artists such as Papa Wemba, Youssou N'Dour, Lokua Kanza and Paul Simon.
Five Alive consisted of Victor Seii, Bob Kioko, Chris Kamau, and David Mageria, who was replaced by Joe Kiragu.
In 1996 he performed and appeared in the video for "Get in the Driver's Seat", a song commissioned by the United Nations Drug Control Programme for a highly successful anti-drug campaign spanning 20 countries.
During his years at Berklee, Wainaina and his band traveled around the country to perform, as well as holding regular shows in Boston.
In order to do this, he made sure that he released a new track every time he returned home for vacation, This was well received by his growing fanbase, with his performance at Kenya's Beats of the Season concert in December 2000 being watched live by 15,000 fans and broadcast nationally.
After the 1998 terrorist bombing in Nairobi where over 200 Kenyans died, "Daima Kenya" was adopted as the unofficial song of mourning, receiving extensive radio and TV airplay nationwide.
This became "Ukweli", a call for justice despite efforts that were being made to cover up the true nature of Father Kaiser's death, which was reported as suicide despite strong evidence to the contrary.
In 2001, Africa Almanac.com listed him amongst the top 100 Africans of the year 2000, which included high-profile names such as Nelson Mandela, Joseph Kabila, Yash Pal Ghai, Baaba Maal and Ousmane Sembène.
In December 2004 Wainaina premiered a 21- song musical theater piece, Lwanda, Man of Stone, based on a local folk story.
A contemporary adaptation of this musical, Lwanda-A Ghetto Story had a very successful run at the GoDown Arts Centre, Nairobi, in December 2006.
He has also written the music for Owen and Mzee, an upcoming documentary about the touching story of an unusual friendship between a tortoise and a baby hippo at the Kenyan coast.
Wainaina also performed at the inaugural Nairobi-hosted North Sea Jazz Festival in February 2006, and at the Netherlands-based version of the same in July 2006.
Eric Wainaina performed during Mata Amritanandamayi's 60th Birthday Celebrations at Amritapuri, Kerala, India on 26 September 2013.