[10] In 2008, Bolling was named a co-host (joining Cody Willard and Rebecca Diamond) of Happy Hour, a market commentary show in the 5 p.m. time slot.

He then went on to also criticize Obama for allowing rapper Common to appear in the White House a few weeks before, exclaiming "it's not the first time he's had a hoodlum in the hizzouse."

Progressive group Media Matters criticized Bolling, saying "Calling the president of Gabon and Common 'hoods in the hizzy' is not colorful commentary, it is overt racism."

"[12] Media Matters also criticized Bolling for his on-air promotion of citizenship conspiracy theories about Barack Obama ("birtherism") and conspiracy theories about the murder of Seth Rich, as well as for his claim in 2011 that "liberal Hollywood was using class warfare" in a Muppets movie "to brainwash our kids" and his claim in 2012 that "Every terrorist on American soil has been a Muslim.

"[13] In 2017, Bob Beckel said that Bolling and Roger Ailes saved his life after performing the Heimlich maneuver on him at a restaurant.

[19] In April 2017, as part of prime-time lineup changes with Bill O'Reilly's exit, Fox announced that The Five would be moving to the 9 p.m. time slot.

Fox News Specialists was created to replace The Five in the 5 p.m. time slot, with Bolling serving as a co-host alongside Katherine Timpf and Eboni Williams.

"[23] Bolling's promotion to hosting his own show on Fox News, effective at the beginning of May 2017, was seen as a victory for the Trump White House.

[27] After the article was published a former Fox News guest alleged that Bolling made numerous unwanted sexual advances towards her.

[28] The day after the HuffPost article was published, Bolling was suspended from Fox News pending an investigation, which the network commissioned the law firm Paul, Weiss to conduct.

[42] Bolling began hosting America This Week, which is produced by Sinclair Broadcast Group and carried by their stations as a Sunday morning talk show, in 2019.

[45] In 2020, Bolling conducted an interview for America This Week with Judy Mikovits, a discredited researcher featured in the video Plandemic.

[46] The video promotes baseless conspiracy theories regarding the coronavirus pandemic, and falsely suggests that Dr. Anthony Fauci, the U.S. government's chief infectious disease scientist, "manufactured" COVID-19.

[50] He and his wife Adrienne’s one son, Eric Chase Bolling, died on September 8, 2017, from an accidental drug overdose.