In the second episode of On Brand with Jimmy Fallon, the competition intensified as the marketing contestants faced their biggest challenge yet: creating a campaign for Southwest Airlines. The task focused on promoting the airline’s new cabin upgrades—three extra inches of legroom and the introduction of assigned seating. Contestants had to develop playful and innovative concepts that matched Southwest’s fun and self-aware brand voice. The episode concluded with the season’s first elimination, sending one contender home.
The Southwest Airlines Challenge
The contestants met with host Jimmy Fallon, chief marketing officer Bozoma Saint John, and guest judge Whitney Eichinger, Senior Vice President and Chief Communications Officer at Southwest Airlines. Eichinger set the brief, asking for a campaign that was both “playful and innovative” and supported by a tagline that would build excitement for travelers. The presentations took place in an airplane hangar, raising the stakes for the creatives.
The judges noticed a significant problem as the pitches unfolded: many ideas were surprisingly similar. Multiple contestants presented concepts centered around legs and legroom, making it difficult for their proposals to stand out. Bozoma Saint John pointed out the overlap, noting that the pitches were blending together and becoming less distinctive.
Contestants’ Campaign Pitches
The ten competitors presented a wide range of marketing ideas to the judges. Sabrina Burke opened with a romance-themed concept, offering chocolates and flowers alongside the tagline:
“You had me at more legroom. Assigned seating is icing on the cake.”
Pyper Bleu made a visual impact by dressing as a flower and stepping into a pot to represent a “growth mindset.” Mahiri Takai framed the airline customer as a superhero who had defeated the problem of “no legroom.” Lauren Karwoski envisioned each flight as a kingdom where “your seat is your throne.” Dr. Raj Srivastava kept his message direct with the line: “more legroom, more space, more Southwest.”
Bianca Fernandez structured her campaign around three short stories featuring different personalities who needed something “extra.” BT Hale delivered a presentation filled with what he called “big pitch energy,” which ultimately did not strongly connect with the panel. Meanwhile, Ryan Winn took a memorable risk during his legroom pitch by removing his pants on stage, a gesture that grabbed the judges’ attention and laughter.
From Taglines to Plane Wraps
After the individual presentations, three contestants were selected as project leaders for turning their concepts into large-scale plane wrap designs. The chosen leads were Ryan Winn, Bianca Fernandez, and Mahiri Takai. Their designs had to be striking and immediately understandable from a distance.
Ryan’s team decorated the aircraft fuselage with various illustrated legs placed beneath the windows to emphasize the extra legroom. Mahiri’s group used bold comic book imagery to bring his superhero concept to life, portraying passengers as heroes. Bianca’s team developed a “space” theme, transforming the plane into a rocket with astronaut imagery. However, the judges found this approach potentially confusing for customers, as it did not clearly communicate the airline’s specific new amenities.
The Season’s First Elimination
After judging the performances from both the initial pitches and the plane wrap challenge, the panel announced the results. Mahiri Takai’s team was declared the challenge winner, and his teammates advanced safely. The judges then turned to the bottom performers.
Jimmy Fallon and Bozoma Saint John informed BT Hale that he would be leaving the competition. His departure was influenced by his performance in both the Episode 1 Dunkin’ challenge and the current Southwest Airlines campaign. The judges noted that while everyone liked him personally, his ideas did not connect effectively with the brand objectives and failed to stand out among the stronger pitches from his competitors. His elimination reduced the number of contestants from ten to nine.
The episode demonstrated the high-pressure reality of agency life, where even good ideas can fail without uniqueness and strong execution. On Brand with Jimmy Fallon airs on NBC and is available for streaming on Peacock.
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