Jon Favreau, Janeane Garofalo and Sandra Bernhard
Christopher Moltisanti really wanted to get into Hollywood. He tried screenwriting and even acting class. His cousin's girlfriend worked for Jon Favreau and managed to get him onto a New York film set, where Favreau was directing Janeane Garofalo and Bernhard. Chrissie offers up some ad-lib dialog. But before long, his cousin's girlfriend steals his heart and the future director of Iron Man steals his script ideas.
"You're robbing a benefit concert, you know that, right?" Years before he found fame mocking the rich and famous as blogger Perez Hilton, Mario Lavendeira played a college student on the wrong end of a mob-related stickup. In the Season 3 episode, getaway driver Jackie Jr. literally pees himself. Perez actually wrote about the show fairly often, even after it finished, once musing about the series' mysterious finale. And of course, making sure to blog about it when an actor's son got himself arrested.
Years before he was the voice of Lego Batman, Will Arnett fought crime in a different way, starring as an FBI agent on The Sopranos. The future Arrested Development cast member appeared in two episodes as husband to the FBI agent who went undercover to try to flip Adriana, in what became one of the show's saddest stories.
Will Arnett wasn't the only member of the Bluth family to make an appearance on The Sopranos back in the day! Tony Hale played a nurse tending to Uncle Junior in the show's third season, more than ten years before his debut on HBO's Veep.
David Lee Roth
The Executive Game was a high stakes night of poker organized by Tony's father and uncle, which Tony took over and for a brief time, handed to ex-con Feech La Manna. It's the game Tony and Jackie Aprile Sr. once robbed as kids and somehow lived to tell about it. The game is packed with celebrities who made cameos as themselves: NFL Hall of Famer Lawrence Taylor, the late Frank Sinatra, Jr., and none other than Diamond Dave himself, Van Halen frontman and solo artist David Lee Roth. Yeow!
DLR isn't the only singer who showed up on The Sopranos! Future Lady Gaga Stephanie Germanotta was just 15 years old when she made a small appearance in the ninth episode of the third season, The Telltale Moozadell. She's one of the teenaged hooligans hanging out with AJ when they vandalize their high school.
Remember those dream sequences from The Sopranos? There was the food poisoning that gave way to Tony's subconscious telling him that Big Puss had flipped to the feds. The season six episode, Join the Club, where a comatose Tony dreamt he was confused with a salesman named Kevin Finnerty. In The Test Dream, Tony encounters multiple wacked wise guys and other deceased characters from his past: Carmine, Ralphie, Mikey, Richie, Puss, Gloria, even his own father. During the dream, he and Carmela have dinner with Meadow's boyfriend's parents, except they aren't really Finn's parents. They're dead detective Vin and Annette Bening... As herself!
Janice Soprano was but one of many characters who could have used anger management classes, but she actually made it there, albeit by court order. Joining her in those classes? Classmate Evelyn Greenwood, played by Chandra Wilson, who won SAG and NAACP Image Awards for her role on the ABC drama Grey's Anatomy.
Lauren Bacall and Ben Kingsley
The show's sixth and final season made room for some Hollywood crossovers, in-jokes and insults, courtesy of Christopher Moltisanti's ill-advised foray into micro-budget horror movies, inspired by the success of Saw and his love of The Godfather. One such Hollywood moment was the appearance of Lauren Bacall and Ben Kingsley. The episode Luxury Lounge was written by Mad Men creator Matthew Weiner and directed by Danny Leiner, of seminal garage rock band The Flying Guacamoles. We all know how much Little Steven loves garage rock, right?
No raps, no Founding Fathers, no Alexander Hamilton, and no Broadway accolades: Lin-Manuel Miranda's first TV role featured just a couple of lines, with the future Hamilton genius playing a hapless hotel bellman in an episode of The Sopranos final season. Not long after, he turned up in another HBO related property: Sex and the City: The Movie, and two more TV shows: Sesame Street and The Electric Company.
Remember AJ's long hair in the show's final season? Rosie Aprile calls him Fabio. The ladies must've liked it, as he had no shortage of female attention. His date in one episode was none other than Katie Lowes, who we know better as Quinn on Scandal.
Daily Show veteran and comedic actor Aasif Mandvi made an appearance as an emergency room doctor who tends to chief Tony Soprano rival Phil Leotardo in the show's final season, after the acting boss of the Lupertazzi family has pre-heart attack troubles. (Sadly, the veteran Goodfellas actor, Frank Vincent, passed away in 2017.) Those aren't the only future familiar faces that graced the screen on the legendary TV show. Remember sex crazed forensics expert Vince Masuka from Showtime's Dexter? C.S. Lee was one of the attending physicians when Uncle Junior shot Tony. Frank Underwood's Chief of Staff, Doug Stamper? Michael Kelly was agent Ron Goddard on six episodes of The Sopranos. Remember Mikey from season one? Al Sapienza turned up years later on House Of Cards, too, as a teacher's union lobbyist. Before we go, we have to give a shout-out to legendary singer Frankie Valli! Imagine having The Four Seasons and The Sopranos on your resume. Rusty Millio wasn't his first organized crime character: he played a mafia boss in two episodes of Miami Vice and the consigliere of the Gambino family in the TV movie, Witness to the Mob.