Reyes was born in Flushing, a neighborhood in the north central part of Queens. She is of Puerto Rican heritage. She has three older brothers and an older sister, Suzanne.
Lucha Libre USA (2010–2012)
In 2010, Sky was a featured interviewer and has added commentary work for the MTV2 program, Lucha Libre USA: Masked Warriors, a show focusing on the transition of lucha libre and related organizations to the United States. On March 19, 2011, Sky made her professional wrestling debut at a Lucha Libre USA show under the ring name Rebecca Reyes, where she teamed up with Nikki Corleone and ODB against Chrissy Cialis, Jacqueline Moore and Tigresa Caliente. On the June 18 episode of LLUSA TV Tapings, Reyes teamed up with Chrissy Cialis and Vladimiro in a losing effort to Mini Park, Octagoncito and Pequeno Halloween in a mixed tag team match. In October, Reyes lost to Lady Luck in a lingerie match. She would return in 2012 during the second season, mainly teaming with Shane Helms in mixed tag team matches.
Independent circuit (2011–present)
On July 1, 2012, Reby Sky made her independent circuit debut at Extreme Air Wrestling where she teamed with Paul London and Brian Kendrick to defeat Miss Jackie and The World's Greatest Tag Team. In 2012, Sky took on Jayme Jameson for the NWA Mid-Atlantic Ladies Championship on two separate occasions and lost both times. On March 9, Sky was part of an infamous triple threat match which included Brittney Savage and Spyra Andover and was featured on Botchamania. After feuding with Jayme Jameson for several months, Sky finally defeated her at the first Shine Wrestling event, SHINE 1. With being engaged to Matt Hardy, she has appeared at several OMEGA events which Hardy owns. At Family Wrestling Entertainment No Limits Sky lost to Ivelisse Vélez.
Sky began her career in dance, performing nationally with the Amira Mor International Entertainment Company, a bellydance troupe, with whom she also made several bellydance instructional DVDs. In 2005, she held a supporting role in the off-Broadway musical, Secrets of the Desert. The show toured several off-Broadway venues, including the Duke Theatre on 42nd street in Times Square, and the DiCapo Opera House. Other notable venues Reyes has performed at include Queens Theatre in the Park and New York's Radio City Music Hall, where she performed for The Beatles drummer, Ringo Starr.
Soon after her stage work, Sky appeared in various television programs and music videos, including Midnight Spike (Spike TV), Date Patrol (TLC-TV), Faking It (TLC-TV) and Más Maíz, a music video featuring N.O.R.E. and Fat Joe.
In July 2007, Sky was featured in a nude pictorial in Playboy magazine, The Girls of Montauk, shot by Michael Dweck. Sky was also featured in the July 2010 edition of the Playboy Cyber Club as "Cyber Girl of the Week" for the week beginning July 19, 2010 and was later named "Cyber Girl of the Month" for November 2010. Sky has also appeared in GQ, Esquire Magazine, Supermodels Unlimited, and STUFF.
Sky was also interviewed in MTV's True Life: I'm a Sports Fanatic, as the NY Giants Girl, airing on September 19, 2009. The show chronicled her involvement as a fan of the New York Football Giants. She sells a line of football fashion handbags via one of her websites, which also promotes her self-proclaimed NY Giants fanatic status as the NY Giants Girl.
Sky was named Miss Howard Stern TV for the month of December 2009 and was voted by Sirius Radio's Howard Stern fans, as "Miss Howard TV of the Year 2009".
In 2010, an official 3D model of Reby Sky was released at DAZ 3D. The model is compatible with software from DAZ 3D, and Smith Micro Software Inc.
Sky plays herself in the 2013 film "Pro Wrestlers vs Zombies" and battles the undead with her real-life husband Matt Hardy.
In 2008, Reyes was sentenced to probation, a fine, and community service for opposing an officer without violence when police stopped her vehicle because it had a broken taillight in 2007 in Florida.
On January 1, 2014, Reyes and Hardy were arrested at the Hampton Inn in Emporia, VA around 5:45 AM for fighting each other. Both where charged with assault and battery and were released on $3,500 bail. It was reported that Reyes and Hardy filed restraining orders against each other.