Ruiz worked as a sous chef at Dish, a restaurant in Clifton, New Jersey, before being hired as executive chef at Sabor in North Bergen, New Jersey circa 2002. In July 2002, he was hired by the new owner of Stephen's Cafe of North Bergen as a consulting chef for a relaunch of the operation. Ruiz relocated to New York City as the first decade of the 21st century came to a close, working as an executive chef at Son Cubano, a short-lived Cuban restaurant on West 27th Street in Manhattan. The 80-seat restaurant featured live Cuban music and a night club atmosphere.
By 2011, Ruiz was executive chef at Brick Oven in Morristown, New Jersey. Together with his then wife, Marie Riccio, on October 10, 2011, Ruiz opened an Italian deli and cafe, Marie's Italian Specialties, in the Hickory Square Mall in Chatham Township, New Jersey. This cafe was memorably referred to by one food reviewer as "the type of deli you might have visited as a child when visiting your grandmother's house — if your grandmother lived in Hoboken or Jersey City in the 1950s."
It was through this restaurant, and its distinctive food, that Ruiz first made the acquaintance of celebrity chef Guy Fieri. Fieri filmed an episode of his popular Food Network television show Diners, Drive-Ins and Dives featuring Marie's Italian Specialties in October 2012, with an initial air date of January 21, 2013. Fieri would ultimately feature the restaurant twice on the show, boosting the popularity of the nine table deli as well as Ruiz's professional profile. Ruiz was later hired to be a judge on other shows starring Fieri, including Guy's Grocery Games and Guy's Ranch Kitchen.
Ruiz and Riccio subsequently divorced, with Riccio retaining Marie's Italian Specialties following the split. In June 2019, Ruiz opened a new restaurant specializing in authentic Cuban fare, called La Cubana, in the Meatpacking District of New York City. Ruiz held the position of Executive Chef at the new eatery. Through connection to his high-profile friend Fieri, Ruiz would become a frequent guest on the Sirius XM radio show Opie and Anthony and its successor, The Opie Radio Show, along with Sherrod Small and Vic Henley. Following that show's cancellation, Ruiz would continue to be a regular on the Opie Radio podcast until the time of his death.
Ruiz was well known as a judge on Guy's Grocery Games, and he also won the most as a competitor raising money as part of various tournaments.
Loved doing radio with him but loved even more our friendship. The long hilarious knowledgeable phone calls. The long walks home after doing the radio show ending in the middle of Central Park where I would turn left and he right,” Hughes wrote. “As we parted he would shout, “you’re not suppose to make new friends at our age.” Always happy, rarely sad. @VicHenley never had a bad word to say about anyone. His laugh/giggle was so contagious which you wanted to be around. Music knowledge second to none.
O'Neal performed his first stand-up in October 1992 at Estelle's in Boston. He had attended an open-mic night at the venue the week prior to his debut where he heckled a performer, who in turn challenged him to try stand-up himself. Comedian Dane Cook witnessed one of O'Neals earliest sets and noted his "gentle-giant appeal ... He already had an edge, but he was a little more vulnerable". O'Neal developed his act in the Boston area for the next six years, where early on he performed under the name Bruiser O'Neal. In the mid-1990s, O'Neal first met comedian and later close friend Jim Norton.
In 1998, O'Neal relocated to New York City, working regular spots at the Comedy Cellar. In early 1998, he took part in the fourth annual US Comedy Arts Festival in Aspen, Colorado. He then moved to Los Angeles in the hopes of finding greater fame: "I tap danced like you wouldn't believe ... trying to get something. "O'Neal ignored demands from club owners to change his confrontational act and struggled to earn enough money. He was "essentially thrown out of America" and accepted offers to perform in the UK, first by English stand-up John Simmit for a part on his Upfront Comedy circuit. O'Neal worked hard to gain the respect of his peers, which he recalled took several months "for them to go 'Ok, this guy's not playing around'". By mid-1999, O'Neal had headlined a comedy tour of Australia. Between 2000 and 2002, O'Neal performed stand-up across Europe, including spots at the Black International Comedy Awards in London and in Edinburgh, Scotland with comedians Lewis Schaffer and Rich Vos.
In 2006 and 2007, O'Neal joined Opie and Anthony's Traveling Virus Comedy Tour, playing large arenas across the US.
In 2010, O'Neal recorded his first and only hour special for Comedy Central, Elephant in the Room. It originated after comedian Dave Attel had praised O'Neal's material to his manager, who entered discussions with the network about producing one. Despite O'Neal being adamant on filming in Washington, D.C., the network wanted it recorded in New York City and O'Neal eventually agreed. The special premiered on February 19, 2011, with an uncut version released on CD and DVD three days later. O'Neal promoted the special with an interview on Late Night with Jimmy Fallon, his first network television appearance in four years.