| 1987 | Recorded his first nationally broadcast stand-up set on Showtime's Comedy Club Network, introducing the 'Uncle Lar'' persona and his rapid-fire one-liner delivery to audiences across the country. |
| 1990 | Appeared on Fox's 'Comic Strip Live' and HBO's 'Opening Night at Rodney's Place,' hosted by Rodney Dangerfield, cementing his reputation as a take-no-prisoners one-liner comic on national television. |
| 1997 | Released the comedy album 'Gimme An "F"' on Discogs, showcasing his politically incorrect 'Uncle Lar'' persona and the signature 'tip from your Uncle Lar'' sign-off that became his trademark. |
| 1999 | Launched his debut live comedy album 'It's a Sick World, I'm a Happy Guy' on Laughing Hyena Records, anchored by his philosophy that in a perfect world, Uncle Lar' would be unemployed. |
| 2000 | Followed up immediately with 'It's a Sick World, I'm a Happy Guy, Volume 2' on Laughing Hyena Records, continuing his rapid-fire commentary on marriage, children, and grown-up misbehavior. |
| 2006 | Auditioned for Season 4 of NBC's 'Last Comic Standing,' advancing to the second round of the quarterfinals and exposing his machine-gun wit to a prime-time national audience. |
| 2008 | Named Chicago Comedian of the Year at the Chicago Music Awards, validating his status as the city's reigning one-liner king and his long-running headlining residency at Zanies Comedy Club. |
| 2009 | Closed out the trilogy with 'It's a Sick World, I'm a Happy Guy, Volume 3' on Laughing Hyena Records, giving Uncle Lar' fans a third chapter of relentless, politically incorrect material. |
| 2021 | Headlined a post-pandemic return run at Zanies Chicago, profiled by Newcity Stage under the headline 'Uncle Larry Reeb Brings His Fusillade of Funny to Zanies,' while continuing as a regular guest on the nationally syndicated 'Bob & Tom Show,' heard in over 100 markets. |
| 2022 | Kept his Midwest circuit firing on all cylinders with consecutive headline dates at Zanies Chicago, Zanies Rosemont, and the Milwaukee Improv, proving Uncle Lar' still draws a crowd after four decades of club comedy. |
Known as “Uncle Lar”, Larry Reeb is the wise-cracking black sheep, politically incorrect relative everyone knows. Uncle Lar’ offers tips on everything from marriage to lotteries to children. Always topping them off with, “That’s a tip from your Uncle Lar’.” Reeb didn’t invent obscene phone calls or adultery, but he makes his living talking about them. In a perfect world Uncle Lar’ would be unemployed. His sharp wit was custom built to handle hecklers. During a performance a regretful drunk once shouted “talk about sex.” Larry retorted, “your parents shouldn’t have had it”, and of course capped it with, “that another tip from your Uncle Lar’. “Uncle Lar’ is a regular on “The Bob & Tom Show,” syndicated in over 100 markets. Larry has been voted Chicago Comedian of the Year, and has made numerous television and radio appearances. Whether he’s headlining comedy clubs, colleges or conventions, his wit is universally appealing. Relatively speaking, everyone travels from everywhere to see their Uncle Lar’.