It’s normal to see a celebrity on any of Woodbine Racetrack’s major days, since the sport attracts people from all walks of life.

Since the late 1990s, and even prior to that, Woodbine has welcomed Olympians, various professional athletes, wrestlers, Hall of Famers, and prominent trainers and coaches in their respective fields, to their major races. And some have stepped out of the role of spectator to take part in the fun and games.

Inviting celebrities to host and make post-positions for the races has always been a way for Woodbine to encourage larger turnouts and to increase interaction from racegoers during the events. Fans want to be where the excitement is, particularly, when their favourite personality makes an appearance. And it definitely doesn’t hurt if they are there to raise awareness about various issues and to help raise money for charities and advocacy groups.

In 2003, eleven World Wrestling Entertainment Inc. (WWE) superstars did just that. They teamed up with Variety, a children's charity dedicated to helping disabled youth, to host at Woodbine for a day.

The 11 wrestlers – namely John Cena, Rey Mysterio and Matt Hardy – participated in an autograph session and a barbecue with fans. They later concluded WWE Day by coupling with the jockeys and their horses for a horse-WWE matchup race. The special drawmasters for that race were: WWE Tag team Charlie Haas and Shelton Benjamin, and fellow WWE wrestler Zach Gowen.

That same year, Canadian figure skater Jennifer Robinson and Canadian professional hockey player and Canada’s flag bearer at the recent Olympic Games opening Hayley Wickenheiser, made quite the duo at Woodbine Oaks. Both Robinson and Wickenheiser have been Olympic representatives, with Wickenheiser making a fifth straight appearance at the Sochi 2014 Winter Olympics.

In 2004, Perdita Felicien, former world champion in the 100m hurdles and retired Canadian hurdler attended the draw for the 145th Queen’s Plate as the guest drawmaster. In addition, Marlene Stewart Streit, a Canadian amateur golfer and a World Golf Hall of Famer, came out for the 2008 Woodbine Oaks draw. The Hall of Famer is also an Officer of the Order of Canada and a member of the Order of Ontario.

Tie Domi attended the 2005 Pepsi North America Cup and Jalen Rose made an appearance at the Pattison Canadian International the following the year. Domi, a retired NHLer, played for the Toronto Maple Leafs at that time. And the retired NBA player and ex-Toronto Raptors player, Jalen Rose, is currently a sports analyst for ESPN.

For the 2006 Woodbine Mile, Ricky Williams, now a retired CFL and NFL player, was the special celebrity drawmaster for that race. And honourary drawmaster Clara Hughes, the only athlete to win multiple medals at both the Winter and Summer Olympic Games, was in attendance for the draw of the 147th running of the Queen's Plate.

The 2007 Pepsi North America Cup made for an interesting but fun pairing, as Matt Stajan and Mayor Hazel McCallion are from two very different professions. Stajan plays for the NHL's Calgary Flames (the Toronto Maple Leafs then,) while Mayor Hazel McCallion is the current mayor of Mississauga, and has been for the last 35 years.

In the following year, then Leafs’ coach Ron Wilson and Don Cherry drew post positions for their events. Wilson, who at the time was the head coach of the Toronto Maple Leafs, attended the 2008 Ricoh Woodbine Mile draw as the honourary drawmaster. And Don Cherry, a retired Canadian NHLer turned hockey commentator for CBC Television, was the drawmaster for the 149th running of the Queen's Plate. Cherry is well-known for his colourful suits and ties and strong opinions.

Chris Bosh, who now plays for the Miami Heat, attended the 2009 Woodbine Oaks draw at WEGZ Stadium Bar in Vaughan, Ont. The ex-Toronto Raptors all-star forward was the drawmaster for the $500,000 race. As well as Gordie Howe, the only player to have a career spanning more than five decades, from the 1940s through 1980s, was the honourary drawmaster for the 150th running of the Queen's Plate in 2009.

Pernell Karl Subban, better known as P.K. Subban, was the drawmaster for the 2010 Pepsi North America Cup. Subban, currently plays for the Montreal Canadiens and is representing Canada at the 2014 Winter Games this month. Later that year, celebrity drawmaster Dion Phaneuf, a Canadian professional ice hockey defenceman and captain of the Toronto Maple Leafs, attended the draw of the 2010 Woodbine Mile.

Micky Ward, often referred to as ’Irish’ Micky Ward, a retired boxer, pulled post positions for the 2011 Woodbine Oaks race. And in the 2011 Pattison Canadian International, Dennis Rodman, the NBA Hall of Famer, funny man and wild card, gave his post picks for the race.

In 2012, Olympic medalist Jennifer Heil, a Canadian freestyle skier from Spruce Grove, Alta, was the guest drawmaster for Woodbine Oaks. Heil is joining with CBC as an analyst for the Sochi 2014 Winter Games, covering the freestyle mogul skiing events. Also participating in the winter games in Sochi as guest host, is Mark Tewksbury, a professional Canadian swimmer, often recognized for his achievements in sport, public speaking, and humanitarianism. Tewksbury was the honourary drawmaster for the 153rd running of Queen’s Plate.