Flynn was created by screenwriter Dan Fogelman and directors Nathan Greno and Byron Howard because they felt that the incarcerated Rapunzel needed someone to escort her out of the tower.

While some reviewers enjoyed the character's refreshing humor, rebelliousness and sarcasm in comparison to traditional Disney princes, others found his personality to be annoying and obnoxious, while panning his narration.

[2] When they were first approached to direct Tangled in 2008,[3] directors Nathan Greno and Byron Howard decided that it would be best "to blow up the scale of the film" and transform it into a "big event", while updating and modernizing the story for a new audience.

[5] However, Greno and Howard decided to make him a thief – dubbed "a subtle yet startling twist for Disney" by The New York Times[6] – to avoid creating a character who is too "safe", opting for a funnier and "edgier" antihero instead.

[7][8] Greno elaborated, "When you look back at some of the past Disney princes ... a lot of them are kind of soft and they're not like people we think are that cool," continuing, "They're good guys, so I guess we sort of took that to the other extreme.

[18] Writing for ReelViews, film critic James Berardinelli felt that the directors' decision mirrored "Disney's approach during the late 1980s and early 1990s, when big name stars were often bypassed in favor of lesser known talents".

[19] Hundreds of actors and singers auditioned and were considered for the role of Rapunzel's love interest,[20] among them comedian Dan Fogler and American Idol alum Clay Aiken.

[24] Describing Tangled as a "very family friendly" version of Romancing the Stone (1984), Levi studied and channelled the film's star, American actor Michael Douglas, and English legend Robin Hood.

"[2] Howard cited American actor Clark Gable and English footballer David Beckham among several celebrities by whom Flynn was influenced during the meeting, joking that the employees eventually "started using Nathan and me as examples of what not to do".

[37] Rob Vaux of Mania.com described the character's relationship with Rapunzel as a "partners-in-crime sort of chemistry, filled with mischief and the odd pratfall while establishing a rhythm wholly their own.

[40] Similarly, The New York Times' Brooks Barnes felt that "Making the leading man an unlikable thief is a subtle yet startling twist for Disney, and Flynn ... is glib in a way that many people now associate with DreamWorks.

There, he is captured and blackmailed by Rapunzel, who hides the crown to convince Flynn to guide her to the floating lanterns in time for her eighteenth birthday, while Mother Gothel, her vain, controlling kidnapper, is absent.

Flynn is pursued by a police horse named Maximus; the vengeful Stabbington brothers, two betrayed accomplices of his; and Gothel, who grows increasingly obsessed with retrieving Rapunzel to continue using her magic hair to stay immortal.

[63] The Houston Chronicle's Amy Biancolli quipped that Flynn's "sensitive chin fur, and the way he talks out of the side of his mouth – makes him look like Dick Cheney at a poetry slam".

[65] Accusing the character of "lacking both superficial and emotional individuality", Jake Coyle of the Southtown Star panned Flynn as "rather obnoxious",[66] Dan Kois of The Village Voice dismissed him as "vanilla".

Writing for the Mountain Xpress, Ken Hanke felt that "what works best is the interplay between the two leads", concluding, "these animated characters are frankly more believable and charismatic than the human ones in ... Love and Other Drugs.

"[73] Sandie Angulo Chen of Common Sense Media wrote that the characters' "relationship is built on mutual respect and trust, something completely missing in many earlier Disney movies.

"[74] The Miami Herald's Rene Rodriquez opined, "Even though they may seem to be boilerplate fairy-tale heroes, you genuinely come to care about Rapunzel and Flynn and root for them to be together,"[75] while Joe Neumaier of the Daily News simply called their relationship "cute".

[76] Ted Fry of The Seattle Times wrote, "The back-and-forth banter of what inevitably becomes a courtship is consistently witty and given extra sparkle from adroit characterizations by Moore and Levi.

[82] Praising the directors' decision to "[bypass] big-name stars in favor of lesser-known talent", TV Guide described Levi's performance as "charming, roguish, and, well, generic enough".

[83] Similarly, Mike Scott of The Times-Picayune wrote that Levi "comes off as an exaggerated, narcissistic version of the rascally Tory Belleci from TV's MythBusters", complimenting the fact that "the cast's names are less than household stature".

[86] Dustin Hucks of Film School Rejects wrote that Levi "creates a significant amount of range and emotion with his voice that truly makes the suave thief with a heart of gold Flynn pop on the screen".

[87] Mathew DeKinder of the St. Louis Post-Dispatch appreciated the comedy in Levi's "quick-tongued delivery",[88] while Rolling Stone's Peter Travers wrote that the actor "does a nice job" as Flynn.

[6][70] Holding Flynn's role and characterization partially responsible for it, they accused the character of being a marketing tool manipulated by Disney to attract larger male audiences via the film's trailers.

[16][63] Writing for the Los Angeles Times, Dawn C. Chmielewski observed that Tangled's marketing campaign involved "amp[ing] up the role of the dashing Errol Flynn-styled male lead to share the spotlight with the golden-haired namesake of the classic Brothers Grimm story".

[44] Richard Corliss of Time mocked the film's marketing and the idea that "The trailers suggest that the movie is an action comedy about a roguish guy ... whose mission is to storm the tower and free the girl inside.

"[105] Similarly, A. O. Scott of The New York Times received Flynn as a "hijacking of a princess's tale", panning the character as "a crude commercial calculation, a sign to the anxious boys in the audience that things aren't going to be too girly, or to Disneyphobes that the studio can bring some DreamWorks-style attitude.

"[69] Claire Martin of The Denver Post felt that Flynn's sole purpose in the film was for potential merchandising opportunities, specifically to "take Ken's role as [Barbie's] male arm candy".

[106] Empire's Helen O'Hara defended Disney's claim "that the new title reflects the fact that [Tangled] is very much a two-hander, with Mandy Moore's innocent but (inevitably) feisty Rapunzel and Zachary Levi's street-wise yet clueless Flynn sharing the lead".

[107] Todd Hertz of Christianity Today observed that "Disney changed the film's title and showcased the swashbuckling Aladdin-meets-Robin-Hood character who replaces the original story's prince", but felt that "Luckily, these marketing moves don't compromise Tangled's phenomenal storytelling or considerable charm.