"I Stoled This Record" followed in 1996. This album, despite not producing a chart single, earned RIAA gold certification for shipping 500,000 copies. This album included parodies of two Shania Twain songs: "If You're Not in It for Love, I'm Outta Here!" became "I'm Not in It for Love, Just Yer Beer" and "Any Man of Mine" became "If Shania Was Mine." John Michael Montgomery's "Sold (The Grundy County Auction Incident)" was parodied twice on this album.

His third album, "Did I Shave My Back For This?" (a take-off on Deana Carter's (Did I Shave My Legs for This?) included his first duet, with Buck Owens on the original track "First Redneck on the Internet." The album also parodied Alan Jackson, Brooks & Dunn, and Mindy McCready.

1998's "Juddmental" was his final album for Razor & Tie. It included a duet, this time with Daryle Singletary on "Ricky Tidwell's Momma's Gonna Play Football," a non-parody song previously recorded by Tim Wilson. This album once again parodied a Twain song, with her "Honey, I'm Home" becoming "Shania, I'm Broke." The Garth Brooks/Trisha Yearwood duet "In Another's Eyes" was also parodied on this compilation.

2000-2005
After leaving Razor & Tie Records, Judd signed to Monument Records Nashville in 2000 to release his fifth album, "Just Another Day in Parodies." This album produced his first chart single in "My Cellmate Thinks I'm Sexy", a parody of Kenny Chesney's 1999 single "She Thinks My Tractor's Sexy" which referenced Chesney's and McGraw's 2000 arrest for stealing a Mounted Reserve officer's horse. The parody charted at 61 on Billboard Hot Country Singles & Tracks (now Hot Country Songs). Following this song was another chart single, "How Do You Milk a Cow" (based on Toby Keith's "How Do You Like Me Now?"), which peaked at 67. In 2002, he released "Cledus Envy," followed later that year by a Christmas album entitled Cledus Navidad. At the end of the year, Judd also made an appearance in the music video for Keith's "Who's Your Daddy?."

His last release for Monument was a six-song EP called "A Six Pack of Judd," released in 2003. After Monument closed its Nashville division, he signed to Koch Records Nashville to release a second EP, the four-song "The Original Dixie Hick," later in 2003. This release, which contained parodies pertaining to the Dixie Chicks, also produced his third chart single in "Martie, Natalie and Emily (The Continuing Saga Of)," a parody of Brad Paisley's "Celebrity."

His final release for Koch was 2004's "Bipolar and Proud." This album produced two more chart singles for him, including his highest-peaking, the 48 "I Love NASCAR", which parodied Toby Keith's "I Love This Bar" and included guest vocals from Keith himself. Following this song was the 58 "Bake Me A Country Ham," based on Tracy Lawrence's "Paint Me a Birmingham."

2006-Present
By mid-2005, Cledus had announced plans to release a tribute album to Ray Stevens entitled "Boogity, Boogity" - A Tribute to the Comedic Genius of Ray Stevens, containing covers of Steven's material with several guest vocalists. Due to the closure of Koch's Nashville division, however, this album was delayed until 2007, when he signed to Asylum-Curb Records and released it in August. Shortly before its release, he made his sixth chart appearance with the non-album song "Illegals". 

Cledus re-signed to Koch in 2009. In January of this year, he released the single "Waitin' On Obama" (a parody of Brad Paisley's "Waitin' on a Woman") referencing Barack Obama's election as President of the United States. This is the first single from his forthcoming album Polyrically Uncorrect. 

He has also signed a publishing deal with Sony/ATV Music and Rascal Flatt’s Joe Don Rooney’s publishing company as a songwriter. Cledus was co-writer on a bonus track “The Way” from the Rascal Flatts CD Still Feels Good. 

Radio and Television Work
Cledus has toured as an emcee with such acts as Brooks and Dunn, Brad Paisley, Trace Adkins, Toby Keith, the Dixie Chicks, Shania Twain, and Montgomery Gentry. His television work includes a stint as the co-host of CMT Most Wanted Live from 2002 to 2004 and as a "special correspondent" on the 2005 season of Nashville Star. Additionally, he was one of the featured contestants on Season Five of VH1's reality show Celebrity Fit Club.

He also hosted the Cledus T. Party Morning Show for WQYK in Tampa, Florida. In January 2008, he returned to Atlanta as the morning host at 94.9/The Bull, WUBL.

Cledus is currently living happily in Georgia with his wife Amy, daughter, Caitlyn Rose and son C. J.