In his three-year-old season, Smile won in the Carry Back Stakes before moving on to Arlington Park.
Smile then won the Grade III Fairmount Park Derby, setting a new track record for 9 furlongs with a time of 1:49.0.
Smile won the race, equaling the stakes record set the previous year by Precisionist.
"[3] A week after his fourth-place finish in the Gulfstream Park Breeders’ Cup, he was shipped back to his place of birth, Tartan Farms, to take over at stud for his sire, In Reality, who was getting on in years.
While he produced stakes winners in the colt Smiling Time and the filly Lavender, he was not a major success and was eventually relocated to a more modest farm in Texas.
In 2004, Smarty Jones (son of Smile's daughter I'll Get Along) won the Kentucky Derby and Preakness Stakes.