From cockpit to canvas: Lt. Col. Bailey's legacy at Mobility’s Hometown

  • Published
  • By Ilona Valence
  • 97th Air Mobility Wing Public Affairs

On April 15, 2024, Retired U.S. Air Force, Lt. Col. Herbet “Bert” Bailey, visited the C-141 Starlifter aircraft memorial at Altus Air Force Base, Oklahoma for the first time to view his artwork displayed on the memorial.

Bailey was greeted with nostalgia and pride as he viewed the memorial at Wings of Freedom Park. While he may have felt a connection to the memorial as a former C-141 pilot, this moment was even more special for him as the monument features his own artwork etched into the stone as its centerpiece.

During his service, Bailey was known in the Air Force as a C-141 and C-17 Globemaster III aircraft pilot, though, he is likely better known for his artistic talents that include the famous illustration titled, “Top Floor, Last Room on the Left.” Although that is the official name of the artwork, the piece is often referred to as “The Last Bag Drag.”

The illustration features a military member in a flight suit walking away from the viewer. The member is depicted a little more tired and a little more worn down from the grind of another mission well accomplished. The Airman wears no rank or patches to make the artwork universally relatable within multiple aviation career fields.

The artwork has come to symbolize the end of one’s time in the Air Force, oftentimes used when commemorating an aircrew member’s career at the time of retirement or a final flight. Like the C-141 memorial, the artwork according to Bailey, was chosen because it perfectly embodies "service before self," the end of the mission, and a job well done.

During his recent visit to Altus, Bailey reminisced over his career, and when asked about his favorite memories from his time in the Air Force, he noted that the top of his list would include the late nights and camaraderie experienced at Charlie's Lounge, at Altus AFB.

“It was probably the best point in my career,” Bailey stated. “When you live here you find things to do, and I had a whole bunch to do.”

He attributes many of those memories to Retired Col. Edward Smith Brannum, former 97th Air Mobility Wing commander. During Bailey's time stationed at Altus AFB, Brannum was the wing commander and was looking for ways to revitalize the officer's club on base.

The then Capt. Bert Bailey was not shy in expressing his thoughts, and with wing commander approval, he started shaping the original version of Charlie's. Bailey's artwork, as well as a giant propeller he brought into the original building, are still enduring fixtures that can be seen in the most recent iteration of Charlie's today.

Bailey is remembered not only for his combined 33 years of service in the Air Force and Air Force Reserves, but for his lasting impression, now memorialized on the base. Though much time has passed since those late nights at Charlie's, the memories of his days at Altus – and the legacy of "The Last Bag Drag" – remain etched both in his heart and on Altus Air Force Base.