He’s also made appearances as a lovable toy cowboy, a laundress from a Broadway musical, a famous pirate, the front man for a well-known American rock band, and more.

It’s Halloween, and Gary has taken his costume game to the next level, spurred on by Southwest Founder Herb Kelleher’s love for celebrating the holiday with Employees. “Herb set a really high bar when it comes to Halloween,” Gary said.

Halloween is an all-out, all-in celebration at Southwest. Teams work together to compete for the honor of producing the year’s best spooky (or kooky) skits and short films. Employees pitch ideas for Gary’s costumes and eagerly await the big reveal. Over the years, local celebrities have judged costume contests at Headquarters. Ticket counters and gates are transformed into magical portals, and uniformed Employees can get creative with approved holiday accessories.  

While the Halloween celebrations have evolved in recent years, photos from the 1970s show gypsy Flight Attendants (known as Hostesses then) posing with a vampire, and a cowgirl Ticket Agent wrangling Customers—proving that the Fun-LUVing Attitude toward Halloween has a long and festive history. “When I joined the Company in the 1980s, it was in full swing. You were just sort of expected to join in the fun,” Gary said.

Halloween is an all-out, all-in celebration at Southwest. Teams work together to compete for the honor of producing the year’s best spooky (or kooky) skits and short films. Employees pitch ideas for Gary’s costumes and eagerly await the big reveal. Over the years, local celebrities have judged costume contests at Headquarters. Ticket counters and gates are transformed into magical portals, and uniformed Employees can get creative with approved holiday accessories.  

While the Halloween celebrations have evolved in recent years, photos from the 1970s show gypsy Flight Attendants (known as Hostesses then) posing with a vampire, and a cowgirl Ticket Agent wrangling Customers—proving that the Fun-LUVing Attitude toward Halloween has a long and festive history. “When I joined the Company in the 1980s, it was in full swing. You were just sort of expected to join in the fun,” Gary said.

The Company’s Dallas offices have traditionally transformed on October 31. Employee Teams spend months planning decorations for their departments, and children and families spend the whole afternoon on site to experience the magic of Halloween at Southwest.

Full-scale celebrations like Halloween are more than just a good time for Employees—they’re an important part of what Southwest calls “Celebrate with Heart,” a way of making the Values and Heart of the organization visible. They also serve as an opportunity to interrupt routines and encourage creativity. In an organization where whole-hearted effort and unconventional thinking are highly valued, celebrations are indispensable. 

Halloween may be one of Southwest’s signature events, but other holidays are celebrated with equal enthusiasm. St. Patrick’s Day parades in Chicago and Dallas have drawn participation from Southwest Employees. Valentine’s Day honors “Heroes of the Heart,” a celebration of behind-the-scenes workers most Customers never see. Employees nominate Teams or departments for the award, and the recipients are kept under wraps until Valentine’s Day. In typical Southwest fashion, there is a big announcement, with the honored group having its Team name proudly displayed on the nose of an aircraft for a year bearing the Heroes of the Heart insignia.

In the early years of Southwest, when the Company grew too large to hold just one Christmas party, Southwest threw three. And when it became too overwhelming to host three parties in December, Leaders started holding Christmas parties at other times of the year. Christmas carols in July? Why not? The parties were such a success that the Company continued hosting them at additional times throughout the year. They eventually became known as Spirit Parties and then simply Southwest Parties.

Not every celebration is a planned event. Small and spontaneous celebrations are equally as important.  As with everything at Southwest, there’s a method to the madness. Halloween (and other) celebrations not only help People enjoy what they do, they interrupt the routines and traditional thought processes and serve as the ultimate Team-building exercise. They encourage People to be more creative and to feel comfortable trying new things, and it’s a day when Leaders step back and take direction from Employees.