The band's subsequent two studio albums, Losing Streak (1996) and Hello Rockview (1998), were released on a major label, Capitol Records, leading to increased exposure.

The band's fifth studio album, Anthem (2003), was the group's most commercially successful to date, featuring the singles "She's Gonna Break Soon" and "The Science of Selling Yourself Short".

Fiorello was replaced by former Teen Idols drummer Matt Yonker, who contributed to the band's ninth studio album, Silver Linings (2020).

A seven-song EP, Uncharted, was released in November 2024 and produced by Jason Livermore and Bill Stevenson of Descendents and Black Flag.

[4] After practicing with a different bass player for a couple of weeks, the band met Roger Lima, a guitarist who also attended the University of Florida.

Over the first few years, the band put out its first EP, Better Class Of Losers, made compilation appearances, and released several vinyl records (featuring songs that would later appear on the 1995 Losers, Kings, and Things We Don't Understand compilation), before Mike Park agreed to release the band's debut album on Dill Records.

[6] After recording what would be Borders & Boundaries, the band opted to buy out its contract from the major label and release the album on Fat Wreck Chords instead.

In October 2000, the band released Borders & Boundaries, and landed the opening spot on Bon Jovi's North American tour.

Shortly after the album's recording, Derron Nuhfer left the band (going on to join Gunmoll and later Escape Grace), and Less Than Jake found a replacement in former Spring Heeled Jack saxophonist, Pete Wasilewski.

Less Than Jake re-released its compilation album, Goodbye Blue and White, which included various 7-inch releases spanning from 1996 to 2001, and provided a different track listing from the first pressing.

The band also held the opening spot on the main stage during the Projekt Revolution tour in the summer of 2004 with Linkin Park, Korn, Snoop Dogg, and The Used before taking a long break to write the group's next record.

After spending the majority of 2005 writing and recording, the band opened 2006 by going on a full U.S. and Europe tour that also featured Catch 22, A Wilhelm Scream, The Loved Ones, The New Mexican Disaster Squad, Rock-n-Roll Soldiers, Damone, Dropkick Murphys, and Far From Finished.

In April 2006, the band released its four-song Absolution for Idiots and Addicts EP, with the group's next full-length, In with the Out Crowd, following a month later on Sire Records.

On May 21, 2007, after much speculation, Vinnie Fiorello announced on his blog that the band had asked and been granted its release from its contract with Sire Records and Warner Bros.

During the 6 Albums / 6 Shows / 6 Nights in London, Chris stated that Less Than Jake's new record label in the UK and Europe would be Cooking Vinyl.

In summer 2007, Less Than Jake embarked on the Shout It Loud Tour, co-headlining with Reel Big Fish and featuring support from Streetlight Manifesto and Against All Authority.

Reissues of Goodbye Blue And White, Pezcore, Losers, Kings And Things We Don't Understand, and the DVD The Peoples History Of Less Than Jake were released on March 18.

[9] Upon talking about the group's new album, Vinnie mentioned his desire to "combine third wave ska and pop punk in each song,"[9] hinting at a possible return to the band's older sound.

On October 12, 2010, the group released TV/EP, consisting of sixteen covers of television theme songs in the span of thirteen minutes: "Spanning from the vintage adverts of yesteryear to the frenetic promos of modern day, TV/EP reimagines a world where pop punk and ska is the music de rigueur, and this is the soundtrack to your couch potato life.

On June 20, 2011, the band released an EP entitled Greetings from Less Than Jake, which was made available on the group's online store and was sold on Warped Tour 2011 as well.

On April 17, 2013, Less Than Jake announced through its Facebook page that the band had signed back to Fat Wreck Chords and would release its first album full of new material since 2008 sometime in the Fall.

[17] On July 29, 2016, at Vans Warped Tour 2016, Peter "JR" Wasilewski told Fuse, "We're working on a new record right now, nothing to really speak of, but it will be coming out in 2017 for sure.

"[18] Less Than Jake launched a tour with Pepper in the January and February 2017 to promote their latest release, the Sound the Alarm EP.

Roger Lima noted: "It was a fairly smooth transition having long time friend and LTJ workhorse Matt Yonker jump on the drum kit late in 2018.

"[21] In October 2020, Lima reflected on Fiorello's departure: "He was the primary lyricist for the band, and it took a bit of refocusing of creative juices as the rest of us took on that role as part of the songwriting, absolutely.

In 2022, Less Than Jake and Bowling for Soup performed over forty shows as part of their Back for the Attack Tour, which also featured The Aquabats on some dates.

[23] On November 15, 2024, the band released a seven-song EP, Uncharted, produced by Jason Livermore and Bill Stevenson of Descendents and Black Flag.

He contributed one track to the Drive-Thru Records tribute to Bob Dylan, under the name "The Stay at Home Joneses", which also featured secondary vocals by Roger.

In 1996, Vinnie, Chris, and Roger served as backup musicians for Asian Man Records owner Mike Park in The Bruce Lee Band (former sax player Derron also provided horns on some of the tracks).

Buddy is one half of Coffee Project along with Jake Crown, who released a self-titled album on the aforementioned Paper + Plastick label.