O-Town's Career in Photos, from “Making the Band” to Their Reunion and Beyond

Take a look back at the early 2000s boy band's reality TV beginnings, their breakup, solo efforts and more

Among the boy bands of late ’90s and early 2000s, O-Town stands out. They may have been something of a flash in the pan compared to the likes of the Backstreet Boys and *NSYNC — their heyday lasting a mere three years — but Ashley Parker Angel, Jacob Underwood, Erik-Michael Estrada, Trevor Penick and Dan Miller delivered time-tested radio hits like “All or Nothing.”

And they were unique in that they existed at the nexus of both the boy band craze and the early reality TV boom, their formation and early success documented in the first three seasons of Making the Band.

As Dirty Pop: The Boy Band Scam — a new documentary series delving into the life and crimes of Lou Pearlman, the infamous talent manager and convicted scam artist behind O-Town, the Backstreet Boys and *NSYNC — streams on Netflix, take a look back at the band’s career, from Making the Band to their 2013 reunion and beyond.

2000: 'Making the Band'

The first season of ABC’s Making the Band tracked O-Town’s formation, as Lou Pearlman chose Ashley Parker Angel, Jacob Underwood, Erik-Michael Estrada, Trevor Penick and Ikaika Kahoano from among eight finalists following a nationwide talent search. Kahoano left the band midway through. Angel, Underwood, Estrada and Penick chose Dan Miller to join the band as Kahoano’s replacement, and the remainder of the season documented the recording of O-Town’s self-titled debut album.

The band returned for two subsequent seasons, which aired on MTV, following their rise to fame and early success.

2000: O-Town Releases Their Debut Single, 'Liquid Dreams'

O-Town’s debut single, “Liquid Dreams,” was released on Oct. 1, 2000. The song reached No. 10 on Billboard’s Hot 100 chart in the U.S.

2001: O-Town Releases Their Self-Titled Debut Album

Three months later, in January 2001, O-Town’s self-titled debut album dropped. It would eventually be certified platinum in the U.S.

2001: O-Town Releases 'All or Nothing'

In March 2001, O-Town released their second single, “All or Nothing.” The inescapable ballad reached No. 3 on Billboard’s Hot 100 chart, becoming the band’s biggest hit, and remains a radio staple to this day.

2001: A Teen Choice Awards Win

O-Town scored two nominations for 2001 Teen Choice Awards, beating out the likes of Nelly Furtado and Dido to win the award for Breakout Artist at the Aug. 12 ceremony.

2001: O-Town Opens for Britney Spears

O-Town hit the road in late 2001, opening for Britney Spears on the pop star’s Dream Within a Dream tour.

2002: O-Town Releases Their Second Album, ‘O2’

With their sophomore album, O2, released in November 2002, O-Town tried to evolve their sound beyond slick teen pop. But singles like “These Are the Days” didn’t have the same impact as “All or Nothing.”

2003: O-Town Breaks Up

With the underperformance of O2, O-Town was dropped by record label J Records in 2003, and Angel, Underwood, Estrada, Penick and Miller disbanded to pursue solo careers.

2005: Jacob Underwood Releases a Country Music E.P.

After O-Town’s breakup, Jacob Underwood formed a country music band, Jacobs Loc. The band released an eight-track E.P., titled simply The E.P., in 2005.

2005: Dan Miller Releases a Solo E.P.

That same year, Dan Miller released his own solo E.P., the pop-rock tinged Slower Than a Gun.

2006: Trevor Penick Releases Solo Single 'Hold On'

In the years following O-Town’s break-up, Trevor Penick tried to carve out a new niche for himself, performing as Tre Scott. He released on solo single, “Hold On,” in 2006.

2006: ‘There & Back: Ashley Parker Angel’

In 2006, Ashley Parker Angel returned to O-Town’s reality TV roots, appearing alongside then-fiancée Tiffany Lynn and the couple’s newborn son Lyric in the MTV series There & Back: Ashley Parker Angel.

Like Making the Band, the show followed Angel’s efforts to launch his own solo career while also documenting his family life. Angel released his first solo single, “Let U Go,” in February 2006 during the show’s run.

2006: Ashley Parker Angels Releases a Solo Album

Two months after the March 13 finale of There & Back, Angel released his debut solo album, Soundtrack to Your Life, in May 2006.  

2007: Ashley Parker Angel Hits Broadway

In 2007, Angel joined the cast of the Broadway production of Hairspray, playing teen heartthrob Link Larkin.

2011: O-Town Gets Back Together … Without Ashley Parker Angel

In a January 2011 tweet, Jacob Underwood teased a potential O-Town reunion. As reports that the band was back in the studio together and planning to tour emerged, Ashley Parker Angel released a statement to TMZ saying that while he was “intrigued” by the prospect of rejoining O-Town, he’d ultimately decided against it.

2014: O-Town Releases ‘Lines & Circles’

The recently-reconstituted O-Town — consisting of Underwood, Estrada, Penick and Miller — released “Skydive,” their first single in over a decade, in May 2014. The song was followed in August by their long-awaited third album, Lines & Circles.

2014–2017: O-Town Hits the Road

O-Town toured consistently from 2014 to 2017, playing both solo shows and alongside other acts like 98 Degrees and Ryan Cabrera as part of nostalgia tours like My2K and I Love the 90s.

2017: O-Town Releases More New Music

In April 2017, O-Town announced a new single, “Empty Space,” which was followed in August by a four-track E.P. titled Part 1. The band continued to tour through 2018, joining the Pop 2000 Tour alongside the like of Aaron Carter and Ryan Cabrera.

2017: Asheley Parker Angel Joins the Cast of 'Wicked' on Broadway

Meanwhile, Ashely Parker Angel continued to build his Broadway cred. After playing Fiyero in the 2014–2015 national touring production of Wicked, he joined the Broadway cast of the hit musical in the role in 2017.

2019: O-Town Releases Their Crowdfunded Fourth Album

Without a label to fund their fourth album, in September 2016 O-Town turned to their fans, launching a Kickstarter campaign that raised more than $81,000 for the project. In August 2019, O-Town released The O.T.W.N. Album, while continuing to tour on their own and as part of the Pop 2000 Tour.

2019: Jacob Underwood and Erik-Michael Estrada Comment on Lance Bass’s Lou Pearlman Doc

In 2007, Lou Pearlman was arrested and charged with conspiracy, money laundering and making false statements during a bankruptcy proceeding. The charges were related to what has been described as one of the largest Ponzi schemes in American history in which he swindled earnings from the pop acts he managed. He was convicted the following year and died in federal custody in 2016.

Nearly three years later, former *NSYNC member Lance Bass produced The Boy Band Con: The Lou Pearlman Story. The documentary featured interviews with several members of the boy bands Pearlman managed, including Ashley Parker Angel, detailing how his actions affected them.

In the film, Angel commented that at the time O-Town worked with Pearlman, it was “sort of out there that Lou had this dark quality to him where he would use his power and influence to try to manipulate young performers into these really questionable scenarios,” and claimed he and his bandmates were warned that there were rumors that Pearlman “might have a thing for boys.”

In July 2019, O-Town’s Jacob Underwood and Erik-Michael Estrada commented on the doc in an interview with PEOPLE. Estrada noted that Pearlman’s story had not previously been told “through the voice of the guys in the bands,” and suggested that the doc gave the boy banders an opportunity “to sort of tell their version of the story.” But he also admitted that he and his bandmates remained grateful that Pearlman brought O-Town together.

Underwood, meanwhile, took issue with the fact that the doc didn’t make it clear that O-Town’s contracts helped them avoid Pearlman’s misdealings, which were already becoming apparent after the Backstreet Boys’ Brian Littrell sued him in 1998.

2023: Ashley Parker Angel on 'The Masked Singer'

As his former bandmates have continued to tour, Ashley Parker Angel most recently appeared on the 10th season of Fox’s The Masked Singer last year.

2024: O-Town Continues to Tour

This year, O-Town was once again part of the Pop 2000 Tour. The band played dates alongside Ryan Cabrera, LFO and BBMak from March to mid-July, and they’re set to play more shows beginning in August and including several dates celebrating the 10th anniversary of their comeback album Lines & Circles this fall.   

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