Timothy Dalton is now in the sixth decade of his professional career. Known first in Britain as a Shakespearean stage actor, and then internationally as James Bond, Dalton continues to adapt, and has found new audiences on television, streaming, and in voiceover work. With such a long career and dozens of on-screen appearances, it is difficult to narrow the list, but here are our choices for Timothy Dalton’s best performances.

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9 Flash Gordon (1980)

     Universal Pictures

Trained as a theatre actor, when Timothy Dalton did take a part in a film, it was usually a classical adaptation, such as Wuthering Heights in 1970 and Mary, Queen of Scots in 1971, both of which could have made this list. So, 1980’s campy space opera Flash Gordon was quite a departure. Dalton plays Prince Barin, jealous of Princess Aura’s love for Flash and forced to fight Gordon in an iconic scene. But by the end of the film, the two are friends and Barin replaces the evil Ming the Merciless as the new ruler alongside Aura. In retrospect, as a royal yielding a sword and delivering some of the movie’s best lines, maybe it wasn’t such a departure after all. Now a cult classic, it did well in the United Kingdom from the start, and reportedly was one of Queen Elizabeth’s favorite movies!

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8 Hawks (1988)

     Pinewood Studios

Between his two turns as James Bond, Dalton took on a very different role as one of two terminally ill patients in Hawks. His co-star Anthony Edwards was best known at the time for Revenge of the Nerds and Top Gun, still a few years before his long run on ER. Together their characters find friendship and even humor as they make the most of their remaining time. Based on a story written by Barry Gibb of the Bee Gees, the film has largely been forgotten. However, it is worth noting as another example of Dalton’s range and willingness to take on challenging roles.

7 The Rocketeer (1991)

     Walt Disney Studios Motion Pictures

Though it was thought at the time that Dalton would return as James Bond, he instead took on the part of a villain, movie star Neville Sinclair, who is secretly a Nazi spy, in The Rocketeer. The film had a long and troubled road to the screen, including multiple re-writes, and received mixed reviews upon release. But Dalton is clearly having fun channeling Errol Flynn. More recently, fans got an animated television series spin-off aimed at young children, but it was canceled after a single season. Still, like many Disney properties of the era, a sequel is supposedly in the works.

6 License to Kill (1989)

     Metro-Goldwyn-Mayer

Dalton’s second and final appearance as James Bond was in 1989’s License to Kill. While his debut in The Living Daylights had clearly changed the tone of the series, this time Dalton’s Bond was even darker and more violent. While those qualities would be praised in Daniel Craig’s debut as the character 17 years later, audiences apparently weren’t yet ready. License to Kill faced other obstacles as well. It had to compete directly with summer blockbusters Indiana Jones and the Last Crusade and Tim Burton’s Batman, resulting in disappointing box office business. Still, Dalton was set to return for a third Bond film, and it went into early development. But by the time MGM finally settled a long legal dispute related to the franchise and was ready to move forward some 5 years later, Dalton was no longer interested.

5 Hot Fuzz (2007)

     Rogue

You can tell when Timothy Dalton is having fun on-screen; there’s a sparkle in his eyes. Such is the case in Hot Fuzz, where Dalton plays supermarket manager Simon Skinner. Not exactly the film’s villain, Skinner is more of a distraction, though still a man with secrets, and Dalton nails his overconfidence. He even gets to briefly break the fourth wall. Reviews were overwhelmingly positive, and remain among the highest for films in which Dalton has appeared.

4 Toy Story Franchise (2010-2019)

     Disney–ABC Domestic Television

Unquestionably handsome, even in his 70s, Dalton continues to appear as a leading man. So audiences might be surprised to learn that he also played a stuffed hedgehog wearing lederhosen! Yes, Timothy Dalton voiced Mr. Pricklepants. First introduced in Toy Story 3 in 2010, Dalton reprised the role in several Toy Story Toons, the television specials Toy Story of Terror! and Toy Story That Time Forgot, and most recently the sequel film Toy Story 4 in 2019. Pricklepants takes his role as an actor seriously, much like Dalton, who must have enjoyed the voice acting experience, as he also performed Lord Milori in the Disney Fairies Secret of the Wings film in 2012.

3 The Living Daylights (1987)

For a certain generation, ask about Timothy Dalton and the response will likely begin with The Living Daylights. The 1987 film cast Dalton as a new James Bond for the first time in 14 years. After Roger Moore quit (or possibly was fired), producers wanted Pierce Brosnan to take over, but he couldn’t due to his commitment to the series Remington Steele. Following a protracted search, Dalton was eventually offered the role. In fact, he had been considered as far back as 1969, when he might have taken over from Sean Connery, but he thought himself too young.

When he finally accepted, Dalton brought a very different sensibility to Bond. Where Moore had been humorous and his films increasingly filled with gags and spectacle, The Living Daylights returned to a more grounded, even reluctant Bond. As might be expected for such a big change, reviews were mixed, though the film’s reputation has grown over the years.

2 The Lion in Winter (1968)

     AVCO Embassy Pictures

Dalton’s performance as King Philip II in The Lion in Winter is remarkable. It was his film debut; he was only 22 years old, and he was sharing the screen with film legends including Peter O’Toole and Katharine Hepburn. But Dalton held his own, and though he had studied theatre in his youth, it was only after this film role that he was signed to the Royal Shakespeare Company. Roger Ebert suggested newcomer Dalton deserved an Oscar nomination, though sadly, 54 years later, he has yet to receive one.

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1 Penny Dreadful (2014-16)

     Showtime

Despite so many diverse projects over the years, Timothy Dalton was synonymous with James Bond for far too long. That began to change in 2014 when he was cast as Sir Malcolm Murray in Showtime’s series Penny Dreadful. Finally, here was the opportunity for Dalton to put his vast experience to use, and he did, fully developing his character in all 27 episodes across 3 seasons. Introduced as an adventurer determined to rescue his abducted daughter, Dalton was praised by critics and fans from the start.

Frustratingly, just as in film, industry recognition never came. The show was unexpectedly canceled, and never received Emmy nominations in any main categories. TV Guide called it “the Most Underappreciated Show of the 2010s.” Still, it kept Dalton in the spotlight, and he has gone on to feature in another series, Doom Patrol. Happily, this means a new generation of fans is likely to recognize him from these shows.