Social media and stand-up comedy Hilarious started her comedy career in stand-up. Delores Shante of
The St. Louis American reviewed her 2017 stand-up performance in
St. Louis negatively, writing, "Jess found out the hard way that poppin' off on celebrities for 60 seconds and engaging an audience... for a full-length routine, are night and day." In 2018, Hilarious had more than four million Instagram followers. She co-hosted the BET Social Awards with
D.C. Young Fly in March 2019.
Television and film After
Nick Cannon direct messaged Hilarious, she made her television debut on his
MTV series ''
Wild 'n Out in 2017, on which she appeared for three seasons. She made her television acting debut on the Fox sitcom Rel''—which premiered in September 2018 and was named after and starred comedian
Lil Rel Howery as Rel—playing Brittany, Rel's stubborn best friend. Anna Moeslein of
Glamour described Hilarious's as a
breakout role, writing that she "steals the show", while
Deciders Joel Keller praised her in a review of the show as "elevat[ing] every scene she was in" and "grounding the show in some realism". The series was cancelled in April 2019 after its first season. Hilarious also starred in the 2019 film
I Got the Hook-Up 2 as Officer Keisha. She later claimed in 2023 that she had not been properly compensated by
Master P for her role in the film. She later starred in the 2023
BET+ biographical film First Lady of BMF: The Tonesa Welch Story, which was
Vivica A. Fox's directorial debut and premiered in October of that year, and as Leah in the drama film
I Hate I Love You, which was directed by Jabriel McIntosh and released in late 2024. premiered in 2020 as part of the launch lineup of
Charlamagne Tha God's Black Effect Podcast Network. It was one of the first podcasts to be released by
Facebook as part of their in-platform podcast streaming service in June 2021. The podcast was hosted at the
Roots Picnic in 2022 as part of their Podcast Stage. By 2023, the podcast was part of the
iHeartPodcasts network and had entered its third season. Hilarious appeared on the scripted,
Kym Whitley–helmed
Audible podcast
Kym, which premiered in October 2022. She guest co-hosted the radio show
The Breakfast Club several times throughout 2023, including during a December interview with
Sexyy Red during which the rapper confronted her over her alleged "sneak dissing". She also had a brief feud with
Lil Meech and his then–girlfriend
Summer Walker after calling Lil Meech "deli smelly" and a "cheater" on the show in June of that year. She announced at a party in Baltimore in December 2023 that she had been hired as a permanent host of the show, replacing
Angela Yee, who had left the show in August 2022. It was officially announced in a video on
The Breakfast Clubs social media accounts in January 2024 and she began her tenure on the show the following month. She announced later that month that she was pregnant with her second child and went on maternity leave that summer, picking producer Loren LoRosa to fill in for her "Jess with the Mess" segment.
Loren LoRosa feud Following Hilarious's return to
The Breakfast Club in November 2024, LoRosa stayed on the show and began hosting her own segment, "Latest with Loren". Social media users largely praised LoRosa's role on the show and compared it favorably to Hilarious's, with some saying LoRosa exhibited more professionalism than Hilarious. Partly in response to comments made by comedian
Corey Holcomb, who criticized Hilarious as untalented and opined that LoRosa was a better fit for the show, Hilarious stated in an Instagram Live stream in March 2025 that she had not been made aware of plans to add LoRosa as a fourth co-host, that she was upset that "Latest with Loren" had been pushed into the time slot originally reserved for "Jess with the Mess", that the show was being run "like a high school", and that she did not receive support from her co-hosts in the face of hate comments.
Blavitys Arielle Poteau and
Essences Jasmine Browley both described Hilarious's behavior, particularly her telling LoRosa to "shut up" due to her "overtalking", as unprofessional, and her anger toward LoRosa as "misplaced", while social media responses were polarized and compared the discussion to a
human resources meeting. Later that month, Hilarious and LoRosa sang and released a parody of the
Brandy and
Monica song "
The Boy is Mine" titled "The Job is Mine", which spoofed their feud over Hilarious's position on the show and was praised by commenters. ==Personal life==