Bob Ryan is a minor recurring character in the HBO series Entourage and had a cameo appearance in the 2015 follow-up film of the same name.
First appearing in the season 3 episode "I Wanna Be Sedated," Bob Ryan is depicted as an open, friendly, sympathetic and kind, but also talkative when it is most needless, out-of-touch, old-fashioned and longtime has-been, legendary movie producer with a 50-year-old career in the motion picture industry and iconic Oscar-winning movies, such as The Network, The Sting, and Dog Day Afternoon, to his credit; he also (by his own account) locked Dennis Hopper in a bathroom, full of hallucinogenic mushrooms, in 1968, inspiring him and thus giving him the idea for his directorial debut, the 1969 independent drama classic Easy Rider, starring Hopper, Peter Fonda and Jack Nicholson.
Years have taken their toll in Bob. He is now a washed up ageing producer, who is long past his glory time and nearly forgotten; in Bob's words, he will not be remembered for the many classics he produced but will instead be remembered for producing the notorious, negatively-received 1995 box office bomb Cutthroat Island, should he pass away any time soon.
Determined to restore his former status as a major player in Hollywood and relieve his old glory days, Bob arrives at Ari Gold's agency and meets with Ari and Eric Murphy, agent and close friend/manager of Vincent Chase respectfully, telling the two he has a script and is interested in making a movie with a star in the main role. Because Eric previously insulted Ari, Ari gets his revenge by referring Eric to Bob, knowing fully well about Bob's eccentricities and endless talk.
Eric has lunch with Bob at Bob's luxurious home, which he bought against the advice of Steve McQueen in the 1960s and which was supposedly visited more than on one occasion by legend Marlon Brando because of Bob's maid. After much talk on Bob's part and a discreet phone call to Ari by Eric about his doubt that Bob has a script, Bob admits he doesn't have a project but proposes (against E's will) that the two stay and think of a project all day in Bob's home. After E sees a framed photo of Bob with Joey Ramone, Bob gives E a script for I Wanna Be Sedated, a biographical movie about the punk rock band the Ramones which Ryan never managed to bring to fruition because of the appearance of the Doors and Morrison's death; E, Vince and Ari become interested in the script as Vince has the once in a lifetime opportunity to perform Joey Ramone on screen.
It appears to be a promising project for Vince, but in the episode "What About Bob?" E, Ari and Bob fail to sell the script to potential studios because Bob would not stop talking and continues to make nonsensical proposals that start with "What if I told you..." and end with "is that something you might be interested in?". E and Ari successfully pitch the script to Paramount, but due to Ari's lack of respect, mockery and contempt for Bob and his tricking Bob into going to Disney while he and E sell the script to Paramount earlier, the humiliated veteran producer sells the script on his own to Warner Brothers.
in "Sorry, Ari", Ari finds out from Dana Gordon that Warner Bros. studio president Alan Gray, with whom Ari and Vince have bad blood since the Aquaman 2/Medellin schedule fiasco in the previous season, will make sure Vince is not involved in the project and the film never to be made, so he tries to convince Bob not to sign a perks package that would finalize the sale, in the process telling him it was Dana who told him Alan won't make the film and also giving Bob a leased car.
Ultimately, the confused Bob follows his "instincts" and signs the deal, also telling Alan that Dana spoke behind his back and causing her contract termination. Bob calls Ari telling him he is sorry and Ari replies he is sorry as well. Ari's mishandling of the Ramone film is the catalyst for Vince temporarily firing Ari before he re-hires him again later in the season.
In the season 5 episode "ReDOMption," Bob joins Ari in a golf game against Gray and Phil Mickelson, during which he demonstrates his ability to get under Ari's skin and openly mocks him, causing him on one occasion to miss a hole. As the four men play, Bob tries to pitch a romantic golf comedy script to Alan, after he tells Alan they make the Ramones film first, still unaware that Alan has no intention of making the film. Bob then witnesses Alan defeating Ari in golf and his loud rants to Ari about how much he hates both Ari and Vince, which cause Alan a heart attack. Despite Bob and Mickelson trying to help Alan by telling him to hold on and Ari calling an ambulance, Alan later dies.
- Season 3 - I Wanna Be Sedated; What About Bob?; Sorry, Ari
- Season 5 - ReDOMption
- Entourage (film) (cameo)
- He was played by late Hollywood legend Martin Landau, who received an Emmy nomination for his performance.
- He is known for his memorable cult catchphrase: "What if I told you (insert exaggerated promise), would that be something you'd be interested in?"
- Bob Ryan is shown to be fond of his catchphrase and takes offence when someone interrupts him mid-way while he says it or when his phrase is mocked; when Eric interrupts him and finishes the phrase, an unimpressed Bob says "Don't be a wise ass" and when Ari, who is understandably angry about Bob ruining the sale of the Ramone script with his constant talk, says in a pitched voice: "I've got a 22 inch c**k. Would that be something you might be interested in?", followed by Bob angrily asking if Ari is mocking him.
- In the beginning of the first episode of Season 4, Welcome to the Jungle, Eric's reference book for production is shown, titled "Is that something you might be interested in?", subtitled "From one of Hollywood's most prolific producers", by Bob Ryan.
- Bob Ryan is allegedly based on real-life Hollywood producer Robert Evans. Evans turned down HBO's offer to play himself in the series, but allowed his home to be used for filming and be depicted as the residence of Bob Ryan.