Trained by three-time Derby winner Bob Baffert and ridden by Garrett Gomez, Lookin At Lucky drew the No. 1 post - generally considered a disadvantage because horses charging into the first turn of the 1 1-4 mile track tend to jam the inside.
Sidney's Candy, 5-1, didn't fare much better, drawing the outside No. 20 post - making for the widest of all trips around Churchill Downs.
Twelve horses have won from the No. 1 post; the last was Ferdinand in 1986. Only two winners have come from No. 20, with Big Brown doing so two years ago.
Devil May Care is a 10-1 co-third favorite as. The last filly to run in the Derby, Eight Belles, finished second two years ago, but broke down after crossing the finish line and had to be euthanized.
Mike Pegram, co-owner of Lookin At Lucky, still feels, well, pretty lucky.
"If there's a horse that can overcome that spot, it's Lucky," he said. "I don't want to sound overconfident, but we got the best jockey in the country and he knows what his responsibilities are."
Trained by John Sadler, Sidney's Candy is ridden by Joe Talamo and owned by weight loss maven Jenny Craig. The colt swept the California preps but has never raced on dirt before.
Devil May Care will take on the boys from the No. 11 post. The other co-third choices are Florida Derby winner Ice Box and Gotham winner Awesome Act.
Devil May Care is one of four horses in the field trained by Todd Pletcher, who is 0 for 24 in the Derby. His best horse, Eskendereya, was forced out with a leg injury last weekend.
Devil May Care has the lowest odds of Pletcher's four horses. Super Saver is 15-1, Mission Impazible is 20-1, and Discreetly Mine is 30-1.
"I came out pretty good in all cases," Pletcher said. "The only negative is the 11 because she'll be in the gate for a long time."
A year ago, 50-1 shot Mine That Bird stunned the field and won under a rail-hugging ride by Calvin Borel, who rides Super Saver this time.
There are a quartet of horses at 50-1 this time: Dean's Kitten, Make Music for Me, Backtalk (a son of 2004 Derby winner Smarty Jones) and Homeboykris, co-owned by Los Angeles Dodgers manager Joe Torre.
Hall of Famer trainer D. Wayne Lukas, a four-time Derby winner, will saddle Dublin, listed at 12-1.
The Derby field in post-position order with odds: Lookin At Lucky, 3-1; Ice Box, 10-1; Noble's Promise, 12-1; Super Saver, 15-1; Line of David, 30-1; Stately Victor, 30-1; American Lion, 30-1; Dean's Kitten, 50-1; Make Music for Me, 50-1; Paddy O'Prado, 20-1; Devil May Care, 10-1; Conveyance, 12-1; Jackson Bend, 15-1; Mission Impazible, 20-1; Discreetly Mine, 30-1; Awesome Act, 10-1; Dublin, 12-1; Backtalk, 50-1; Homeboykris, 50-1; and Sidney's Candy, 5-1.
The draw reverted to a traditional pill pull for the first time since 1997, after a two-tier, made-for-TV process was used the last 12 years.
Instead of the connections for each horse selecting their starting spots, officials pulled entry blanks simultaneously with a numbered pill to determine what spot a horse breaks from in the starting gate.