It was created by the same people behind Pardon the Interruption (PTI), on which Le Batard has appeared multiple times as a substitute host.

The arrangement became necessary after Bomani Jones, who had joined the show in 2013, relocated to New York to co-host High Noon with Pablo S. Torre.

After March 2020, during the COVID-19 pandemic in the United States, Jones made frequent co-host appearances (and occasionally acted as Dan's substitute host) from home via Zoom split-screen tele-conferencing, along with other frequently recurring ESPN personalities Pablo Torre, Mina Kimes, Katie Nolan, Israel Gutierrez, Elle Duncan and Domonique Foxworth.

Highly Questionable emanated from ESPN's studio at the Clevelander Hotel in South Beach, where Le Batard's radio program is also broadcast.

The show, and the introduction of Le Batard's father Gonzalo to the project, was part of an effort by ESPN to attract more Latino viewers.

[7][11][12] Beginning in 2012, other ESPN personalities including Bomani Jones and Bill Simmons appeared as contributors to the show.

[8][13][14] On May 13, 2013, Le Batard got a second co-host when frequent guest Bomani Jones, who had been based in North Carolina, joined the now-renamed Highly Questionable.

[15][16] In June 2017, Le Batard said that was the moment the show found its footing, as Jones' addition helped it gain enough viewers to avoid what was considered to be a near certain cancellation.

On March 23, 2015, Highly Questionable was moved from ESPN2 to ESPN weekdays at 4:30 PM Eastern, leading into sister shows Around the Horn and PTI.

[17][18] In May 2017, ESPN announced that Jones would leave HQ in June 2017 while a new show featuring him and Pablo S. Torre (titled High Noon) was developed.

Until the final episode on September 10, 2021, the show continued with several ESPN correspondents, including Torre, Jones, Domonique Foxworth, Monica McNutt, Elle Duncan, Clinton Yates, Sarah Spain, Mina Kimes, Katie Nolan, Mike Golic Jr. and Israel Gutierrez, as they questioned and discussed sports issues from their own homes, and/or its studio complexes.

[21] Throughout its run, Highly Questionable needed to employ guest hosts whenever Le Batard was unavailable, such as when he took time off for his wedding and honeymoon.

Jon "Stugotz" Weiner, Le Batard's radio co-host, would frequently fill a slot, as would Miami-based journalists like Israel Gutierrez.

Beginning in the 2019 football season, ESPN's Monday programs began carrying a football-centric series of topics, including Le Batard and Papi broadcasting from Miami with two guest contributors.

[2][3][4][5][8] In late summer 2014, the show moved to a new set on the second floor of the Clevelander Hotel in Miami's South Beach.

Occasionally, Dan and Papi found questions humorous or ignorant enough in nature that they were not worth answering, and just simply laughed instead.

Juanito took bets on virtually any sporting event known to man, from the America's Cup to middle school basketball.

Papi was also known to thank Juanito for a tip he allegedly had given him or implying that he had had a role in a certain event's outcome, including horses crashing at the finish line of a race, or other bloopers.

[24] Special guests have included Lil Wayne,[24] Pat Riley, Jason Taylor, Kimbo Slice, Sebastian the Ibis, NBA Hall of Famer Isiah Thomas, Ron Magill, Steven Bauer, Pedro Martínez, Micky Arison, Mike Lowell, Lil Dicky, Robert Smith, and Pat Sajak, among others.