‘Blue Bloods’ Once Featured an ‘Entourage’ Star: Here’s Who

by Taylor Cunningham

Blue Bloods has seen its fair share of celebrity guest stars over the years. But do you remember when Johnny Drama brought his hijinks to the Reagans? We do, and we think he deserves a few more cameos in the future.

In 2017, Kevin Dillon, famous for his spot on Entourage, appeared in the CBS drama as Jimmy O’Shea, Linda Reagan’s troubled brother.

His first episode was season 7’s Hard Bargain. Jimmy showed up in Danny’s life after he was arrested for breaking and entering. And, of course, he asks his sister’s well-connected husband for help.

At first, it seems that Jimmy was a typical burglar. But after some convincing, he finally admits that he actually got himself mixed up with the mob. He was in the house trying to hide out—not steal precious valuables. And eventually, the situation turns dangerous for Danny and Linda.

Because Jimmy winds up staying with his sister, the mob members turn their attention to Danny’s house. And they’re unwilling to keep Jimmy safe when they have three kids at home.

By the end, Jimmy realizes that the only way to solve the problems is to confront the goons. When he does, he takes a beating. But he luckily escapes alive.

Jimmy O’Shea Returns to ‘Blue Bloods’ the Following Year and Once Again Confronts the Mob

The following season, Jimmy shows up for a second Blue Bloods episode. And once again, it’s to pull his sister and brother-in-law into trouble.

In Close Calls, Jimmy attempts to pull off massive credit card fraud using Danny and Linda’s names—and Linda had only just lost her life. So Danny was particularly enraged to learn that Jimmy would use her in the scheme. So when Danny finds out what his degenerate brother-in-law did, he goes to great lengths for payback.

To do that, Danny and Baez force him to make nice with some Albanian mobsters they’re after. And once Jimmy scores a meet and greet, he has to sit down wearing a wire. Of course, the encounter turns deadly fast.

However, Jimmy proves that he’s not a lost cause when he sticks with the operation and helps bring down the criminals, which almost leaves him dead.

After showing some bravery, he redeems himself with the audience and Danny. As the episode ends, Danny begrudgingly admits that he has some respect for Jimmy O’Shea, and they part on good terms.

Unfortunately, we haven’t seen the Entourage star reprise his role. But because Blue Bloods loves a good mob plot, there’s a good chance that he’ll end up at Danny’s house at least one more time.