Seventeen years on, a bald and rather more sedate Agassi will take centre stage this week when he steps on court at the Stella Artois Championships to contest the 1,000th match of his career.
Few could emulate the Las Vegas showman, be it in the fashion stakes, the showbiz lifestyle, or the rollercoaster career.
Agassi has had it all -- the Grand Slam wins, the top ranking, the low ranking and even the occasional controversy.
Through it all, he has remained one of the most gifted and popular players ever to pick up a tennis racket.
Rarely has a player managed to chalk up as many column inches as Agassi has done during his 999 matches to date.
Touted as a champion from the moment he dazzled his way into the French Open semi-finals at the age of 18 in 1988, Agassi had to wait another four years before getting his hands on a Grand Slam trophy.
While his initial lack of success kept him off the back pages of the newspapers, the showman provided enough fodder to warrant front-page treatment.
A tennis player with the looks and groupies of a rock star, Agassi created a skirmish at Roland Garros in 1990 with what he called his "lycra, hot lava look".
Philippe Chatrier, then president of both the French body and the International Tennis Federation, was not impressed with Agassi's neon-look cycling shorts and shirts and threatened to ban outlandish outfits at the tournament.
"I think you should have freedom to express what you feel. Wearing colours is what tennis needs. Without colours I'd still be me but I'd be more boring."
Unhappy with Wimbledon's all-white dress rule, Agassi boycotted the event for three years, declaring he did not possess any suitable attire for the championships.
Reacting to the furore created by Agassi's wardrobe, his fellow player Mats Wilander of Sweden said: "It's the first time I've seen a tennis player with that attitude.
"I think it's great, but I think it's going to be tough
When Agassi did finally turn up at the All England Club in 1991, the unveiling of his staid, all-white garb was once again headline news.
But while Agassi was happily playing to the crowds, his younger American rivals Pete Sampras, Jim Courier and Michael Chang were walking away with the honours.
Realising that he was being left behind, the 22-year-old Agassi started embracing all things traditional and made his breakthrough at Wimbledon in 1992.
But discovering the winning formula -- Agassi also captured the US Open in 1994 and the Australian Open in 1995 -- did nothing to dampen his off-court exploits.
His union with Shields proved to be an on-court disaster. The American's career spiralled out of control as his ranking plummeted to a dismal 141.
With pundits ready to write his tennis obituary, Agassi employed drastic measures to arrest the fall and started playing in the lowly ITF Challenger circuit.
Although his stint at the Challenger events allowed Agassi to regain his confidence and winning touch, his marriage fell apart and ended in divorce after just two years.
No longer distracted by the Hollywood scene, Agassi was determined to return to his glory days.
Gone was the on-court clowning. Instead Agassi adopted a steely mindset every time he faced an opponent.
A mature and more philosophical Agassi finally completed his Grand Slam journey in 1999 by winning the French Open, becoming only the fifth man to have taken all four major titles.
Agassi increased his Grand Slam tally to eight titles by lifting the Australian Open in January before briefly reclaiming the world number one ranking.
Even though his American contemporaries have given up the rigours of trying to stay on top, the 33-year-old Agassi continues his quest to increase his title haul.
Now married to former women's number one Steffi Graf, Agassi no longer craves publicity.
When Agassi steps on to the grass of Queen's Club for match number 1,000, he will want his tennis to do the talking.