1987 was a breakthrough year for Lara, when in the West Indies Youth Championships he scored 498 runs breaking the record of 480 by Carl Hooper set the previous year. He captained the tournament-winning Trinidad and Tobago, who profited from a match-winning 116 from Lara.

In January 1988, Lara made his first-class debut for Trinidad and Tobago in the Red Stripe Cup against Leeward Islands. In his second first-class match he made 92 against a Barbados attack containing Joel Garner and Malcolm Marshall, two greats of West Indies teams. Later in the same year, he captained the West Indies team in Australia for the Bicentennial Youth World Cup where the West Indies reached the semi-finals. Later that year, his innings of 182 as captain of the West Indies Under-23s against the touring Indian team further elevated his reputation.

His first selection for the full West Indies team followed in due course, but unfortunately coincided with the death of his father and Lara withdrew from the team. In 1989, he captained a West Indies B Team in Zimbabwe and scored 145.

His father died in 1989 of a heart attack and his mother died in 2002 of cancer.

In 1990, at the age of 20, Lara became Trinidad and Tobago’s youngest-ever captain, leading them that season to victory in the one-day Geddes Grant Shield. It was also in 1990 that he made his belated Test debut for West Indies against Pakistan, scoring 44 and 5. He had made his ODI debut a month earlier against Pakistan, scoring 11.

In January 1993, Lara scored 277 versus Australia in Sydney. This, his maiden Test century in his fifth Test, was the turning point of the series as West Indies won the final two Tests to win the series 2–1. Lara went on to name his daughter Sydney after scoring 277 at SCG.

He is the only man to have reclaimed the Test record score, having scored 375 against England in 1994, a record that stood until Matthew Hayden’s 380 against Zimbabwe in 2003. His 400 not out also made him the second player (after Donald Bradman) to score two Test triple-centuries, and the second (after Bill Ponsford) to score two first-class quadruple-centuries. He has scored nine double-centuries in Test cricket, third after Bradman’s twelve and Kumar Sangakkara’s eleven. As a captain, he scored five double-centuries, which is the highest by any one who is in charge. In 1995 Lara in the Test match away series against England, scored 3 hundreds in three consecutive Matches which earned him the Man of the Series award. The Test Series was eventually drawn 2–2. He also held the record for the highest total number of runs in a Test career, after overtaking Allan Border in an innings of 226 played at Adelaide Oval, Australia in November 2005. This was later broken by Sachin Tendulkar of India on 17 October 2008 whilst playing against Australia at Mohali in the 2nd Test of the Border–Gavaskar Trophy 2008.

In 2001 Lara was named the Man of the Carlton Series in Australia with an average of 46.50, the highest average by a West Indian in that series, scoring two half centuries and one century, 116 against Australia. That same year Lara amassed 688 runs in the three match away Test series against Sri Lanka making three centuries, and one fifty—including the double-century and a century in the first and second innings of the 3rd Test match at the Sinhalese Sports Ground, equating to 42% of the team’s runs in that series. These extraordinary performances led Muttiah Muralitharan to state that Lara was the most dangerous batsman he had ever bowled to.

Lara was reappointed as captain against the touring Australians in 2003, and struck 110 in his first Test match back in charge, showing a return to stellar performance. Later that season, under his captaincy, West Indies won the two match Test series against Sri Lanka 1–0 with Lara making a double-century in the First Test. In September 2004, West Indies won the ICC Champions Trophy in England under his captaincy. For his performances in 2004, he was named both in the World Test XI and ODI XI by ICC.

In March 2005, Lara declined selection for the West Indies team because of a dispute over his personal Cable & Wireless sponsorship deal, which clashed with the Cricket Board’s main sponsor, Digicel. Six other players were involved in this dispute, including stars Chris Gayle, Ramnaresh Sarwan and Dwayne Bravo. Lara said he declined selection in a stand of solidarity, when these players were dropped because of their sponsorship deals. The issue was resolved after the first Test of the series against the touring South African team.

For his performances in 2005, he was named in the World Test XI by ICC.

On 26 April 2006 Lara was reappointed the captain of the West Indies cricket team for the third time. This followed the resignation of Shivnarine Chanderpaul, who had been captain for thirteen months—in which the West Indies won just one of the 14 Test matches they had competed. In May 2006, Lara led the West Indies to successful One-Day series victories against Zimbabwe and India. Lara’s team played Australia in the finals of the DLF Cup and the ICC Champions Trophy where they finished runners up in both finals.

On 16 December 2006 he became the first player for the West Indies to pass 10,000 One Day International runs, and, along with Sachin Tendulkar, one of only two players, at the time, to do so in both forms of the game. On 10 April 2007 Lara confirmed his retirement from one-day cricket post the 2007 Cricket World Cup. A few days later he announced that he would in fact be retiring from all international cricket after the tournament.

Lara played his final international game on 21 April 2007 in a dead rubber World Cup game against England. He was run out for 18 after a mix-up with Marlon Samuels; England won the game by 1 wicket. Before the end of this World Cup Glenn McGrath stated that Lara is the greatest batsman that he has ever bowled to.

On 19 April 2007 Lara announced his retirement from all forms of international cricket, indicating that the West Indies vs England match on 21 April 2007 would be his last international appearance. He was run out after a bad mixup with Marlon Samuels for 18, as England went on to win the match by one wicket.

On 23 July 2007 Lara agreed to sign for the Indian Cricket League. He is the former captain of the Mumbai Champs. He volunteered to play for his home team Trinidad during the start of 2008 domestic season. He had not played for Trinidad for the last two years. He made his comeback a memorable one with a match winning hundred over Guyana, followed by a dismissive undefeated half-century in the second innings, scored at over two runs per ball. In the third-round game (Trinidad got a bye in the second round).

On 7 September 2008 he took part in Soccer Aid 2008, and on 6 June 2010 in Soccer Aid 2010, playing for the Rest of the World vs a team of England celebrities and ex-pros. Lara was also a talented football player in his youth and often played with his close friends Dwight Yorke, Shaka Hislop and Russell Latapy while growing up together in Trinidad. Yorke, Hislop and Latapy would go on to play for Trinidad and Tobago at the 2006 FIFA World Cup.

In 2009, Lara was made an honorary Member of the Order of Australia (AM) for services to West Indian and Australian cricket.

Brian Lara is also a golf player. He has participated in golfing tournaments throughout the Caribbean region and has won titles. In September 2009, Lara was inducted as an honorary lifetime member of the Royal St. Kitts Golf Club. He wrote an autobiography Beating the Field: My Own Story co-written with Brian Scovell.

Lara suffered a fractured arm against the Leeward Islands in St Maarten on 19 January, which kept him out of the ICL season. He nevertheless affirmed his commitment to returning to Twenty20 cricket, and on 27 June 2010 appeared for the Marylebone Cricket Club match against a touring Pakistan team, scoring 37 from 32 balls.

Lara is the father of a daughter called Sydney (born 1996) whom he fathered with Trinidadian journalist and model Leasel Rovedas. Sydney was named as a tribute to one of Lara’s favourite grounds, the Sydney Cricket Ground, where Lara scored his first Test century—the highly acclaimed 277 in the 1992–93 season. In late 2010, Lara and Rovedas welcomed another daughter, Tyla.

After expressing his interest to play in the 2011 fourth edition of the Indian Premier League (IPL), and despite not having played active cricket for four years, Brian Lara still managed to attract the highest reserve price of $400,000 ahead of the IPL players’ auction in early January 2011; however, no franchise bought him.

Lara was inducted into ICC Hall of Fame in January 2012.

In 2013, Lara became involved with the Bangladesh Premier League team Chittagong Kings as their ambassador.

In July 2014, he played for the MCC side in the Bicentenary Celebration match at Lord’s.

On 18 November 2016, Brian Lara signed with Newcastle C&S D5’s side The Bennett Hotel Centurions.

The Brian Lara Stadium opened in 2017 was named in his honour in Trinidad and Tobago.