Jon Kelley has built one of television’s most diverse careers, seamlessly transitioning from sports anchor to entertainment correspondent to game show host over the course of more than 35 years. At 60, the Lincoln native continues to thrive as the host of the hit syndicated series “Funny You Should Ask” while expanding into HBCU sports broadcasting and executive producing content for Byron Allen’s media empire.
Early Life
Jonathan Kelley was born on August 5, 1965, in Lincoln, Nebraska, where journalism literally shaped his childhood. His mother, Peggy Kelley, spent over 25 years working at the Lincoln Journal and Star newspaper. She’d often pick up young Jon from school and bring him to the sports department to do homework while she worked.
Can you imagine a better way to absorb the craft? Journalism was essentially in his DNA from the day he was born, with newsroom energy surrounding him throughout his formative years.
Those early experiences around reporters and editors planted seeds that would eventually flourish into a broadcasting career. But first, Kelley had athletic dreams to pursue. Like many Nebraska kids, he grew up loving football and had the talent to match his passion.
Education
Kelley earned a full-ride football scholarship to the University of Nebraska-Lincoln, where he played I-back and running back for the legendary Cornhuskers from 1984 to 1987. Playing for Nebraska during that era meant competing at the highest level of college football, though the team’s national championships would come just after his playing days ended.
He graduated in 1988 with a Bachelor of Arts in Broadcast Journalism, combining his athletic background with his childhood memories of the newsroom. The degree gave him the technical foundation he needed, but his mother’s career had already provided the intangible understanding of what great storytelling looks like. That one-two punch of formal education and informal exposure proved invaluable.
After graduation, Kelley briefly chased his NFL dreams by signing as a free agent with the Denver Broncos. When that didn’t pan out, he pivoted to broadcasting. It turned out to be the best career move he never planned to make.
Career
Kelley’s professional journey began at KTIV-TV in Sioux City, Iowa, where he worked as a weekend sports anchor and reporter. It’s the classic small-market start that countless broadcasters experience, learning on the fly while building a reel. He then moved to KMTV-TV in Omaha before landing at WDAF-TV in Kansas City, where he served as a sports reporter and weekend anchor.
The big break came in April 1991 when WMAQ-TV, NBC’s Chicago-owned and- operated station, hired him as sports reporter and weekend anchor. He was just 25 years old and heading to one of America’s top media markets. By 1995, he’d ascended to lead sports anchor, putting him in the perfect position to cover one of the greatest dynasties in sports history.
Chicago Bulls Era
Kelley anchored sports broadcasts for all six of the Chicago Bulls’ NBA championship seasons between 1991 and 1998. Think about that timing. He was covering Michael Jordan, Scottie Pippen, and Dennis Rodman during their absolute peak, providing nightly highlights to a city obsessed with sports.
His hour-long special on the Bulls’ quest for a fifth championship earned him a Chicago/Midwest Emmy Award in 1997.
He also received the Peter Lisagor Award for Sports Journalism in 1996 and the Illinois Broadcasters Association Silver Dome Award for Best Sports Cast that same year. During this period, he even shared the anchor desk with personalities like Rodman and Jay Leno while hosting “Sports Sunday,” which became WMAQ-TV’s top-rated sports highlights program. Not bad for a kid from Lincoln, Nebraska.
In 1998, Kelley secured early release from his WMAQ contract to join Fox Sports Network. He served as the main anchor for “The National Sports Report” and the lead anchor for the weekly series “Baseball Today” from 1990 to 2001.
Kelley’s career took an interesting turn in 2001 when he became the primary correspondent for the syndicated entertainment show “Extra.” He also co-hosted the one-hour weekend edition during a six-year run that lasted until 2007.
His “Extra” success led to co-hosting ABC specials, including “Holiday with the Stars” in December 2007 and an “All-Star Tribute to Movies” on Oscar Sunday. ABC then tapped him to host the fifth and final season of the reality competition series “The Mole” in summer 2008, replacing previous hosts Anderson Cooper and Ahmad Rashad. The show aired on Mondays at 10 p.m., starting May 26, 2008, although it lasted only one season.
Kelley returned to local news in July 2011, joining KNTV-TV in San Francisco as morning co-anchor. After spending two years in the Bay Area, he returned to Chicago in November 2013 to co-anchor “Good Day Chicago” on Fox-owned WFLD-Channel 32. He held that position until June 2016, when the next significant chapter of his career began.
Partnership with Byron Allen and Allen Media Group
The Entertainment Studios partnership, which began in June 2016, has become the most extended and stable phase of Kelley’s career. Byron Allen’s company, now known as Allen Media Group, is the largest producer and distributor of first-run syndicated programming in America. AMG delivers 12 hours of content daily to approximately 1,100 stations nationwide and owns 28 ABC, NBC, CBS, and Fox network affiliate stations.
In February 2024, Kelley signed a multi-year contract renewal that expanded his role as executive producer for television and digital programming. “I’m energized and honored to continue my journey as a part of Allen Media Group’s historic movement and explosive business growth,” Kelley said when announcing the deal. Byron Allen praised him as “an incredibly talented, brilliant, and charismatic television host and executive producer.”
“Funny You Should Ask” Success
Kelley’s flagship show, “Funny You Should Ask,” has become a genuine hit. The comedy game show features professional stand-up comedians, including Byron Allen, Anthony Anderson, Bill Engvall, Vivica A. Fox, David Alan Grier, Tiffany Haddish, Howie Mandel, Jon Lovitz, and Sherri Shepherd, interacting with contestants competing for cash and prizes. Kelley has hosted the show since its fall 2017 debut.
In May 2025, Allen Media Group renewed the series for Seasons 9 and 10, extending it through the 2026-27 season. The show reaches more than 90% of U.S. broadcast markets and airs on major station groups including CBS, Fox, Nexstar, Sinclair, Hearst, and Cox Media Group. It also broadcasts on AMG’s Comedy TV network and the Grio Television Network. Season 9 episodes began airing in September 2025 with Kelley continuing at the helm.
HBCU Sports Broadcasting
Kelley has simultaneously expanded into HBCU sports broadcasting as a colour analyst for football games on the HBCU GO streaming platform. Throughout October 2025, he provided commentary for marquee matchups, including the Las Vegas HBCU Classic, where Grambling State faced Jackson State at Allegiant Stadium on October 25. He also covered the Gulf Coast Challenge between Jackson State and Alabama A&M on October 4.
He hosts “HBCU GO TIME” as well, a weekly digest show covering SWAC, MEAC, and CIAA basketball that launched in November 2022. These games air across HBCU GO, Sports.TV, and CBS-owned and- operated stations nationwide, connecting him to younger audiences and emerging sports media markets.
Other Professional Ventures
Beyond his on-camera work, Kelley co-authored “Breaking Into Broadcasting,” a guide to landing on-air television jobs that leverages his 35+ years of industry experience. He also works with J2 Strategic Communications, training celebrities and athletes on interview techniques and media performance. He’s represented by All American Speakers Bureau and Speaker Booking Agency for corporate events, keynote addresses, and virtual speaking engagements on topics such as broadcasting, career development, sports journalism, and career transitions.
Personal Life
Kelley maintains a significant level of privacy regarding his personal life. He’s married to Milan Kelley, an American actress with credits in “The Gallery” (2013) and “Everything as Is” (2013). Their wedding date hasn’t been publicly disclosed, and the couple keeps their children out of the spotlight.
Standing 6 feet 2 inches tall, Kelley currently resides in Los Angeles with his family. He’s managed to balance a high-profile television career with genuine privacy, which isn’t easy in today’s social media-driven entertainment landscape.
Net Worth
Kelley’s estimated net worth ranges from $1 million to $5 million as of 2024-2025. These figures represent industry-based estimates rather than confirmed disclosures, since Allen Media Group is privately held and isn’t required to report executive compensation.
His income streams include hosting duties for multiple shows, executive producer fees, HBCU sports commentary, media training work, book royalties, and speaking engagements.
Some sources cite salary ranges of $40,000 to $110,500 per year for television journalists, although these appear to be general industry estimates. Given Kelley’s multi-show hosting responsibilities and producing roles, his actual compensation is likely to run significantly higher than these baseline figures.
