- Had actually retired from acting when the creators of "Entourage" first approached him about doing the show. It wasn't until he was informed the part of Eric had been written specifically for him that he decided to take part.
- Good friends with Leonardo DiCaprio and Tobey Maguire.
- Was voted "Most Likely to be Famous" by his high school class.
- Ex-boyfriend of Julianne Hough.
- Was crowned Homecoming King at his high school in 1991.
- Is a fan of the New York Islanders, having grown up on the Islanders' former home of Long Island during the early 1980s when the team won four straight Stanley Cups.
- Is of Irish ancestry.
- Was among the guests at Kevin Dillon's wedding to Jane Stuart.
- His mother died in March 2009 aged 62.
- No relation to Billy Connolly (of "Head Of the Class" fame), despite a popular misconception.
- Born on the same date as Matt Lucas and Eva Mendes.
- Owns the podcast company ActionPark Media (APM) with Narod Michelle.
- Has a daughter Kennedy Cruz Connolly (b. June 2021) with his girlfriend Zulay Henao.
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