Danny Boy (rapper)

In 1990, O'Connor got together with fellow rapper Erik Schrody (Everlast) who had just released a rap album called Forever Everlasting (1990), that didn't have much success. O'Connor knew Schrody when he went to William Howard Taft High School in Woodland Hills, California (1984–1986), and various hip hop event they attended in their teens. Both of Irish American decent, they decided to make a hip hop group with this identity. While hanging out at O'Connor's home, Schrody noticed a cassette with the title House of Pain, which was a demo of a Punk group O'Connor tried to put together. Schrody really liked the name and felt they should re-use as their name. Schrody brought in his former DJ Leor Diamant (DJ Lethal), who actually of Lativian decent, and House of pain was created. While in House of Pain, Danny Boy acted as the hype man, second emcee, art director and the graphic artist of the group.[2] After they recorded a demo, for which O'Connor designed the cover, that created a bidding war among labels. The label they chose was Tommy Boy Records, who credits O'Connor's art work to have initially caught their attention.

In 1992, they released their debut album House of Pain, subtitled Fine Malt Lyrics.[3] Their first single "Jump Around" was a major hit. In the United States, it peaked at number 3 on the Billboard Hot 100, while reaching number 5 on the Hot Rap Songs, 13 on Rhythmic Top 40, 1 on Hot Dance Music/Maxi-Singles Sales, number 17 on the Billboard Dance Club Songs,[4] and is certified platinum.[5] O'Connor expressed regrets for not doing any writing on Jump Around, for the later royalties it could have provided him.[6] Their second single "Shamrocks and Shenanigans (Boom Shalock Lock Boom)", it peaked at 65 on the Billboard Hot 100, 75 on the Hot R&B/Hip-Hop Songs, 14 on the Dance Club Songs, and 74 on Radio Songs. The album peaked at 14 on the Billboard 200,[7] 14 on the U.S. Billboard Top Current Albums,[8] 16 on the U.S. Billboard Top R&B/Hip-Hop Albums,[9] 14 on the U.S. Billboard Top Album Sales,[10] and is certified platinum.[5]

In 1993, O'Connor with his group mates were among the rap artists who had cameo roles in Ted Demme's film Who's the Man?.[11][12] For this project they provided a theme song by the same name, which was also used as a single for the soundtrack and their subsequent album. It rose to number 97 on the Billboard Hot 100, 77 on the Hot R&B/Hip-Hop Singles & Tracks, and 10 on the US Billboard Hot Dance Music/Maxi-Singles Sales.

In 1994, they released Same as It Ever Was.[13] The album peaked at 12 equally on the Billboard 200,[7] the U.S. Billboard Top Current Albums,[8] the U.S. Billboard Top R&B/Hip-Hop Albums,[9] the U.S. Billboard Top Album Sales,[10] and is certified gold.[5]

In 1996, they released Truth Crushed to Earth Shall Rise Again.[14] The album peaked at 47 on the Billboard 200,[7] 47 on the U.S. Billboard Top Current Albums,[8] 31 on the U.S. Billboard Top R&B/Hip-Hop Albums,[9] and 47 on the U.S. Billboard Top Album Sales.[10]

After House of Pain disbanded, O'Connor continued being involved in musical projects and did freelance work such as logo designing, streetwear, and sneakers.

In 2001, O'Connor's next group XSupermodels (XSM) only saw a promotional release for their album Artificial Intelligence. That year, he was the featured rapper in Powerman 5000's remake of the Frankie Goes to Hollywood hit song "Relax", on the Zoolander soundtrack.

In late 2004, the creation of the rap supergroup La Coka Nostra started when O'Connor was mentoring young artists. He took notice of two up and comers which included George Carroll (Slaine) and brought them to meet his former DJ from House of Pain, Leor Diamant, who at the time was working on a compilation album and championing a new artist as well. They decided to make a group and asked O'Connor to become a member as a hype man and art director. After accepting, O'Connor felt that there was a void and asked experienced rapper William Braunstein (Ill Bill) to join. The group's name came about, when O'Connor teased Carroll and Braunstein with that nickname, after they both had a night out. The group started releasing music on MySpace, and went viral. Eventually, O'Connor received a letter from former House of Pain colleague Erik Schrody, who asked if he could join. By 2006, the group consisted of O'Connor, Carroll, Diamant, Braunstein, and Schrody (who left some time after the first album was released).

In 2005, the documentary film Just for Kicks about the sneaker phenomena and history in hip-hop, had its world premiere.[15] O'Connor was among the producers. It won "Best Documentary", and "Best Overall Film" at the USVI Film festival. It was part of the official selection at the Tribeca Film Festival, New York Film Festival, Sheffield Documentary Festival, International Documentary Film Festival Amsterdam, Bangkok International Film Festival, Res Fest, New York Latino Film Festival, San Francisco Black Film Festival, NYC Urban World Festival, and the Leipzig Documentary Festival.[16]

In 2009, La Coka Nostra released "A Brand You Can Trust" was released on July 14, 2009, on Suburban Noize Records.[17] It sold over 500,000 units.

That same year, while touring, they had a three day layover in Tulsa, Oklahoma. O'Connor took advantage of this free time to visit the town and found the location of the house used by the main characters in the filmThe Outsiders (1983). He took a picture, posted it on MySpace, and the photo went viral. This led O'Connor to found The Delta Bravo Urban Exploration Team. With team-members in Los Angeles, Chicago, and New York City, they visit documents notable pop culture landmarks from film, television, music, and true crime.[18] One of their speciality is to show a photo of what the location looks like now to compared it to what it looked like when it was part of something that gained notoriety.[19] Delta Bravo identified locations from movies and television shows including Fast Times at Ridgemont High (1982), Saturday Night Fever (1977), Valley Girl (1983), The Bad News Bears (1976), All in the Family (1971 to 1979), Gilligan's Island (1964 to 1967), etc.[2]

In 2012, separately from The Delta Bravo Urban Exploration Team, La Coka Nostra released their second album, Masters of the Dark Arts.[20] It reached 176 on Billboard Top Current Albums, 40 on Independent Albums, and 31 on Top R&B/Hip-Hop Albums.

In 2016, La Coka Nostra released To Thine Own Self Be True.[21] The album reached 38 on the Billboard Top R&B/Hip-Hop Albums. That same year, the film Let Me Make You a Martyr premiered,[22] in which O'Connor plays a role.[23]

O'Connor, a lifelong fan of S. E. Hinton's book The Outsiders and its film adaptation, opened The Outsiders House Museum in Tulsa, Oklahoma, on August 9th, 2019.[24] Since discovering its location in 2009, O'Connor always had the thought of buying it, which he eventually did in 2015. After raising funds and the community volunteering help the house went through extensive renovations to restore it and maintain its authenticity from the film.[25] Since its opening, the museum now contains a collection of Outsiders memorabilia.[2] For his efforts on the project and his service to the community O'Connor received a key to the city.[26]

In 2021, separately from The Delta Bravo Urban Exploration Team and The Outsiders House museum, O'Connor acted in the suspense film Ida Red.[27] That same year he was a prominent interviewee in Soleil Moon Frye's documentary Kid 90.[28]