Born in the English town of Newcastle-under-Lyme, he joined local club Stoke City's youth team set-up in 1981 before signing professional terms with Stoke's rivals Port Vale the following year.
The club were in the fourth tier of English soccer but by the time Earle left in 1991, they had reached Division Two.
He joined London club Wimbledon in 1991 and played for nine seasons as the small club maintained its Premier League status throughout.
He was part of the so-called 'Crazy Gang' while at Wimbledon - a group of players who were noted for their off-field antics as well as intimidating tactics during games.
It helped them overachieve during their time in England's top division.
Earle was one of the most influential players during this period, scoring 76 goals from 350 appearances in all competitions.
He played at the 1998 World Cup and scored Jamaica's first ever World Cup goal. After retiring in 2000, he moved into the media and has worked extensively in both the UK and USA.
The early years
Born in 1965, Earle attended Longton High School in Stoke-on-Trent and his talent on the soccer field was obvious. It was no surprise when he was taken on as a 16-year-old by local club Stoke City.
Initially a striker, he stayed just one season with the Potters' youth team, however. A broken leg put paid to any hopes of being kept on by the club and he was snapped up by city rivals Port Vale.
Port Vale years
Earle signed for Port Vale in 1982 and made his debut on August 28, 1982 in a 1-0 loss to Swindon Town.
He scored his first goal in a 4-1 win over Aldershot but that was his only goal of a campaign that saw him make nine appearances in all competitions. Vale were promoted to Division Three.
The player saw slightly more game time in the 1983/84 season, with 12 outings but failed to find the net as Vale were relegated back to the fourth tier of English soccer.
He was finally handed a regular first-team spot in the 1984/85 season and responded in style, scoring 15 goals from 46 league games and 19 in all competitions, including a hat trick against Hereford United on February 2, 1985.
Earle matched that total the following campaign as Port Vale finished fourth and were promoted to Division Three.
The player made 142 consecutive appearances between September 1984 and January 1987, with the run only ended due to a groin strain.
He was forced to undergo surgery to fix a hernia early in the 1987/88 season but returned in January 1988 and played in 25 league games, scoring four times.
Robbie Earle, Port Vale, 1989
He was part of the side that beat top-flight club Tottenham to knock them out of the FA Cup that season.
Further success followed as Earle bagged 19 goals in 1988/89 and scored both goals in the two-legged playoff final victory over Bristol Rovers that saw Vale promoted to Division Two.
The midfielder continued to shine in the higher division, scoring 12 goals in 52 games in 1989/90. He added another 11 the following season, which turned out to be his last at the club.
Earle made 357 appearances in all competitions and 294 in the league for his hometown club, scoring 90 goals and helping them move up two divisions. He is considered the best player to have played for the club.
Move to Wimbledon
Wimbledon chairman Sam Hammam persuaded Earle to move to south London in the summer of 1991. The club paid Port Vale £750,000 for his signature and he continued his excellent form in England's top division.
He scored 14 goals in the final season of the First Division and added seven more from 42 appearances in the following inaugural Premier League campaign.
Along with players such as John Fashanu, Vinnie Jones, Lawrie Sanchez, Jason Euell, Dean Holdsworth, Marcus Gayle and Andy Clarke, Earle was part of the 'Crazy Gang' at the club.
They were known for practical jokes in the dressing room and during training and for intimidatory tactics both before and during matches.
Robbie Earle, Wimbledon, 1998
The mentality certainly seemed to work as Wimbledon remained in the Premier League against the odds throughout Earle's nine seasons at the club. He scored 59 top-flight goals and 76 in all competitions from 350 appearances.
He helped them to sixth spot in the table in 1993/94 - the club's best finish in England's top division.
He made just nine appearances in 1994/95 due to injury but was back on the goal trail the following campaign with 11 from 37 league outings. He was also appointed captain ahead of that season.
While holding their own in the Premier League, the Dons put together two fine cup runs in 1996/97.
Having moved to Selhurst Park, Earle captained them to the semifinals of both the FA Cup and League Cup. In February 1997, he won the Premier League Player of the Month award.
He scored seven goals in all competitions in 1998/99, as the Dons reached the League Cup semifinals once again.
However, top-flight survival was a struggle and the following season they were relegated on the final day of the campaign.
Earle sustained a heavy blow to the stomach during a reserve game in 2000 and became seriously ill with a ruptured pancreas. He announced his retirement in November 2000 after 284 league games for the Dons.
International career with Jamaica
Earle enjoyed only a brief international career with Jamaica, making eight appearances for the 'Reggae Boyz'. He was eligible to play for the Caribbean nation due to his parents.
He had hoped to play for England but, after the Three Lions failed to make an approach, he threw his lot in with Jamaica at the age of 32.
Although spanning just eight games, Earle's international career included playing at a World Cup as Jamaica qualified for France 1998.
Robbie Earle, Jamaica, World Cup, 1998
He scored his nation's first ever World Cup finals goal in a 3-1 defeat by Croatia at the Stade Felix-Bollaert. He featured in all three of Jamaica's group games.
They lost 5-0 to Argentina at Parc des Princes but beat Japan 2-1 at Stade de Gerland. It was not enough to seal passage into the knockout stage, however, and they were eliminated after finishing third in Group H.
He had previously made his international debut against Canada on September 7, 1997, playing 15 minutes as a substitute. He only made one start - against Croatia - and his final appearance came in the World Cup win over Japan.
Retirement and media work
After retiring, Earle moved into the media and has enjoyed success in both radio and TV. He has worked for Capital Radio, Radio 5 Live, BBC, ESPN, ITV, Sky Sports and OnDigital.
He has also worked in the written media, producing columns for the London Evening Standard and Stoke-based Sentinel.
In March 2011, Earle became a broadcast analyst for MLS side Portland Timbers and two years' later was a lead studio analyst for NBC Sports' coverage of the Premier League.
Robbie Earle, 2016
He has also worked as a co-commentator on their Match of the Day and Premier League Download programmes.
In June 2010, he was involved in a controversy for giving away World Cup tickets for the Netherlands v Denmark match which were supplied to him by ITV.
It later emerged that ITV had provided him with 400 tickets, with 40 for the final, and he had distributed them to family and friends. A friend then sold them on to a Dutch company for resale.
Even though Earle said he was unaware of his friend's intentions and did not profit from the incident, he lost his £150,000 a year contract with ITV. He also lost his role as an ambassador for England's 2018 World Cup bid. Earle described his actions as "naive".
Personal life
Earle married his wife Sandra in 1999 and the couple have a son named Otis, who is also a professional soccer player. Otis has played in the US for FC Tucson, FC Dallas and Arizona United.
Earle was awarded an MBE in 1999 for his services to the game and was voted into the PFA Fans' Favourites list by Port Vale supporters in 2007.
He was inducted into the English Football Hall of Fame in 2009 as Football Foundation Community Champion. Earle is a vegetarian.
In addition to soccer punditry, he appeared on BBC's Strictly African Dancing as part of Africa Lives season and took part in the 2007 edition of MasterChef. He has also appeared in television commercials promoting blood donation.
Earle forms one half of The 2 Robbies alongside former Middlesbrough player Robbie Mustoe, with the NBC Sports analysts hosting a popular podcast.
In June 2020, he broke down in tears on NBC's Premier League Mornings show when watching footage of the Burnley versus Manchester City match. During the match a plane flew a 'White Lives Matter Burnley' banner over the Etihad Stadium.
Responding to Sky Sports' Mike Wedderburn's condemnation of the banner, he said: "It highlights the complexity of what we're fighting against, the layers that come with the racial issues that we're trying to address."
Clearly emotional, he added: "If we stand together in the fight, we've got a chance."