Raised in Drexel Hill, Pennsylvania, Civillico became enamored with juggling after seeing a street performer in Boston when he was 11 years old.

Reviewers of Comedy in Action generally had positive impressions of his show, praising him for his seemingly boundless energy, his ability to engage the audience, his prowess with making comical off-the-cuff remarks, and his juggling talent.

[10][11] During the visit, he was entranced by a street performer, juggler Peter Panic, at Harvard Square and vowed to become an entertainer.

Selected by Peter Panic as a volunteer, Civillico found himself facing a large group of people, a feeling he said was "one of those defining moments".

[11] In the summer before ninth grade, Civillico competed at the International Jugglers' Association Convention in Pittsburgh and was ranked 14 out of 21 performers who were younger than 18.

[11] Civillico founded the Juggling Club at Saint Joseph's Prep in 1997 when he was a freshman and performed with other members for free at local nursing homes.

In a March 2000 interview with the Delaware County Daily Times, Civillico noted that many people his age were as skilled as he at juggling.

[5] In February 2000, he juggled for developmentally disabled children at Archdiocese of Philadelphia's Don Guanella School,[4] where he is a frequent volunteer.

With Sean McKelvey, his best friend and fellow student at Saint Joseph's Prep, he was hired to do six shows daily from June 25–August 15 and September 1–4.

[19] In October 2013, he was the host of Caesars Got Talent, a fundraising event held to benefit Opportunity Village, a Las Vegas non-profit organization that serves the intellectually disabled.

"[18] When he was 18 years old, he accepted an offer to perform for 50 minutes on a cruise ship that began boarding passengers in Cartagena, Colombia.

Among the lost items were the juggling clubs he had used to win a gold medal from the International Jugglers' Association in 1998 in the junior division.

[22] A January 2009 article in the Orlando Sentinel noted that Civillico performed 200 times every year for Disney Cruise Line and at numerous corporate occasions.

[24] Civillico has performed in Springfield, Illinois;[25] Modesto, California;[26] Springdale, Arkansas;[27] Mohegan Sun Arena, Connecticut;[28] and Tampa, Florida.

[30] In December 2012,[37] Alonzo "Turf" Jones, a hip-hop dancing contortionist who competed on America's Got Talent's seventh season, became Civillico's opening act.

[40] Las Vegas Review-Journal's Mike Weatherford in a June 2012 review called Civillico's early act in the show "one of the most memorable bits".

[41] Civillico selects two male volunteers from the audience ("two strong beasts of men")[24] to assist him to mount his unicycle.

[41] Weatherford described the act as the "dudes (and it would only work with guys) become uncomfortably familiar with both the front and back of Civillico's crotch, before they all help each other mouth-catch marshmallows".

"[30] When a boy urinated in his pants during the show, Civillico, inspired by the comedy film Billy Madison, said, "I pee myself all the time.

Fontein also commented that Civillico's "high side kick followed by an exaggerated wedgie pull" comprised some of his "odd signature moves", making him the "definition of zany" and generating an enjoyable spectacle.

[24] Today in Las Vegas reviewer Laura Damian wrote in February 2013 that he has "the energy of a hummingbird and the comedic timing of a veteran street performer" and "has a way of seamlessly integrating members of his audience into his show in a way that's original, charming and hilarious".

Reviewer Hilary Billings wrote in USA Today: "Praise to Jeff for not only mesmerizing little humans with his mad juggling skills, but for giving the parental units something to laugh about.

[45] Civillico debuted "Juggle-Vision" in June 2014 in which he mounted a GoPro camera on himself to allow viewers to see on a screen what juggling looked like from his perspective.

[45] The pilot episode of Civillico's proposed show on Travel Channel, Vegas Strip Search, aired on April 6, 2013.

[55] The organizations helped by Win-Win Entertainment include the American Cancer Society, The Shade Tree Shelter, St. Jude's Ranch for Children, Nevada Partnership for Homeless Youth, and the Lili Claire Foundation.

Performers and groups participating in the fundraiser included singer and impressionist Véronic DiCaire of Véronic Voices, American Idol's Taylor Hicks, comedy magician Mac King, Divas Las Vegas' Frank Marino, "junk rock" band Recycled Percussion, pop vocal group Human Nature, the Kristef Brothers, and the Las Vegas casts of the musicals Jersey Boys and Million Dollar Quartet.

[57] Win-Win Entertainment organizes multiple shows a week at children's hospitals and other places serving disadvantaged youth.

[55] In 2019, the non-profit organization operated in Las Vegas, Minneapolis, New York City, Orange County, California, Orlando, Florida; Phoenix, Arizona; and Reno, Nevada.

[59] He performed magic tricks to the hundreds of people watching him online during the events and had confetti during a June 2020 show requested by the American Heart Association, which had raised enough funds to meet its set target.

[60] The Las Vegas Sun's Ron Sylvester wrote in December 2012 that Civillico had received "top reviews" from Yelp and TripAdvisor.