On Brand with Jimmy Fallon host faces wild pitches on the show— “Take My Pants Off” among the ideas

Ryan Winn with his "Take off my pants" pitch on On Brand with Jimmy Fallon | Image via Instagram/ @ryanwinn44
Ryan Winn with his "Take off my pants" pitch on On Brand with Jimmy Fallon | Image via Instagram/ @ryanwinn44

Creative tension reached a comedic peak in On Brand with Jimmy Fallon Episode 2 when many competitors submitted nearly similar tagline concepts for Southwest Airlines that emphasized comfort and legroom. When Ryan, one of the competitors, told the judges, "I've gotta take my pants off," in an attempt to stand out from the others, the corporate branding competition swiftly descended into anarchy.

The scene perfectly encapsulated the intense atmosphere of the competition; in accordance with Fallon's agency model, competitors were evaluated not just on their words but also on their level of audacity and creativity. The room erupted in creative risk-taking and limelight anxiety as judges Jimmy Fallon, Bozoma “Boz” Saint John, and brand representative Whitney Eichinger scrutinized each proposal.

One of the most talked-about moments of On Brand with Jimmy Fallon was this strange but unforgettable pitch moment, which highlighted the thin line separating inspiration from imitation. It emphasized that the competitors must push boundaries or risk being absorbed by clichéd concepts.


When creativity collides — The “Pants Off” pitch in On Brand with Jimmy Fallon episode 2 that stood out

After three competitors were placed on almost identical leg-related campaigns, Ryan's frustrated "take my pants off" phrase ended the repetition and the tension. It was a spontaneous act of desperate creativity. More than just making people laugh, it seemed like an appeal to be noticed.

Moments like these are what make On Brand with Jimmy Fallon so unpredictable; one minute, the show is all about branding insights, and the next, you're seeing a contestant rip through every filter in search of a joke. This high-stakes creative show illustrated how fast comedy can become strategy.


Overlapping ideas & the spark that broke through

Lauren was the first one to begin the legroom theme. He started off with the phrase,

“Your flight. Your kingdom. Claim your throne with extra comfort.”

Elijah offered a "leg up" viewpoint, and Azhelle followed with a slogan that included legs wishing for an encore. While praising the humor, Boz Saint John pointed out that the impact was diminished by overlapping concepts.

Ryan acknowledged that his opinions seemed too similar to theirs, so he boldly said,

"I've gotta take my pants off!"

It served as both a humorous release and a reminder that on On Brand with Jimmy Fallon, distinction is priceless. Originality may be dangerous, as evidenced by the judges' emotions, which were half astonishment and half laughing. What began as a silly outburst soon turned into a defining creative move, sparking conversation among both contestants and viewers about how far one should go for originality in branding.


From joke to execution — Did it help or hurt

The judges had to determine whether Ryan's use of visual metaphors incorporating legs in his wrap design was gimmicky or creative. His performance tended toward dramatic flair, but in the end, he needed to convey brand messaging rather than just shock.

Ultimately, the judges assessed both uniqueness and conformity to Southwest's lighthearted, self-aware tone. Ryan was chosen to lead the wrap design phase due to his momentum, although it is still up for debate whether or not he was saved by the decision to "pants off" as a pivot. The episode demonstrated how lighthearted and brutal the show can be when everyone is trying to find new angles.

His concept proved that on On Brand with Jimmy Fallon, clarity and execution are what really determine who wins, even while comedy can draw in viewers. It served as a striking illustration of how brand storytelling requires a harmony between eccentricity and lucidity in order to be effective.


Watch more interesting pitches on On Brand with Jimmy Fallon on ABC.

Edited by Gouri Maheshwari