Lewis was born in Rio Claro, Trinidad. He represented the West Indies under-19s at the 2010 Under-19 World Cup in New Zealand, playing three matches. He had earlier represented the team in the 2009–10 WICB President's Cup, the domestic limited-overs competition.

Lewis made his first-class debut for Trinidad and Tobago in March 2012, in the 2011–12 Regional Four Day Competition. Later in the year, he represented the team in the 2012 Champions League Twenty20 in South Africa, playing a single match (against Sri Lankan team Uva Next).

At the 2013 Champions League Twenty20 in India, Lewis scored 211 runs from five innings, finished as his team's leading run-scorer (and fifth overall). His tournament included scores of 70 from 35 balls against the Titans (a South African team) and 62 from 46 balls in the semi-final against the Mumbai Indians. For the 2014 Caribbean Premier League, Lewis signed with the T&T Red Steel franchise, and scored 321 runs from eight innings (the most for his team, and seventh overall). He switched to the new St Kitts and Nevis Patriots franchise for the 2015 edition, and scored the third-most runs for his team (behind Marlon Samuels and Martin Guptill). Later in 2015, Lewis signed with the Barisal Bulls franchise for the inaugural season of the Bangladesh Premier League. In one match against the Dhaka Dynamites, he scored 101 not out from 65 balls, the tournament's only century. Lewis now represents Dhaka Dynamites in the competition after a blitzkrieg for them in his short stint in the 2016 edition.

In the 2017 Caribbean Premier League, he will for the first time open the batting with his mentor Chris Gayle for an entire season at the St. Kitts and Nevis Patriots which also includes West Indies T20 captain Carlos Brathwaite.

On 3 June 2018, he was selected to play for the Vancouver Knights in the players' draft for the inaugural edition of the Global T20 Canada tournament.

In March 2016, Lewis was added to the West Indies squad for the 2016 ICC World Twenty20, replacing the injured Lendl Simmons. He made his Twenty20 International (T20I) debut on 27 March 2016 against Afghanistan at Nagpur^[12]

In his very second T20I, Lewis scored a blistering century against India in the first match of the series in the USA. He scored the century off 48 balls, which was the second fastest by a West Indian after Gayle and sixth fastest overall. During his innings, he hit 5 sixes off 5 balls in an over bowled by Stuart Binny. He couldn't send the last ball out of the park but made 32 runs(1 run made