1998–2007: Career beginnings Down with Webster originally started as an instrumental jazz band that was formed in a music class at Glen Ames Senior Public School in 1998 by band members Patrick Gillett and Tyler Armes. They, along with the original members of the band, quickly named the group toward the end of class after the beloved
titular character from the 80s sitcom
Webster, who is played by
Emmanuel Lewis. Following a victory at their school's "
Battle of the Bands" competition, the group was joined by Andrew Martino and Martin "Bucky" Seja, students from
Cardinal Carter Academy for the Arts, and other members who attended
Malvern Collegiate Institute. As a
jam band, they made
reggae,
funk and
jazz inspired music in Armes' father garage.
Hip-hop elements were incorporated into their music once Seja became a part of the group and rapped along with Gillett, who also brought an influence of
blues rock to the band. The band released a six-track
CD-R EP titled ''The Reverb Session July '03
. This release was primarily sold at concerts in 2003 and 2004. Hype man Kyle "Kap" Fairlie, a former actor whose voice work includes roles in the Nelvana series Redwall, Franklin, Babar and Rolie Polie Olie, and the film The Little Bear Movie'', and rapper
Cameron "Cam" Hunter would later join the band's lineup.
2008–2012: Time to Win, Vol. I & II The group built a following through their energetic shows. Jill Langlois of
Chart recounted their performance at
Canadian Music Week in March 2008: "...the band exploded onto the stage and never slowed down or stopped. Words will never really describe the Down With Webster experience." She described them as "flashy and obnoxious, but fun and loveable". In June, the group was named 'Best Unsigned Artist in Canada' by
Rogers Mobile and received a recording prize worth $25,000. After facing years of rejection, they captured the attention of music executives including musicians
Gene Simmons and
Timbaland, who wanted to sign the band to their respective record labels. The former had aspirations for them to appear in a reality series to grow their audience as well. According to Timbaland, "That group is the most amazing and creative, innovative group that's going to come out in 2010." Ultimately, they signed with Universal/Motown.
Time to Win, Vol. I was released on October 6, 2009. The lead single from the EP "
Rich Girl$", which sampled the
Hall & Oates track of the same name, peaked at No. 21 on the
Canadian Hot 100. In the fall of 2009, they opened for
Forever the Sickest Kids on the Cheap Date Tour. The follow-up single "
Your Man" peaked at No. 12 on the Hot 100, and was certified double platinum in digital downloads by the
CRIA. The first headlining tour, WINTOUR I, had the band tour Canada and the United States in January and February 2010. The tour started in
Halifax on January 7 and ended on February 1 in
Vancouver. The band also opened for Timbaland on two dates in February on the
Shock Value II Tour. They were nominated for '
New Group of the Year' at the
2010 Juno Awards, losing to
Arkells. Additionally, they received nominations for 'UR Fave: New Artist' and '
Pop Video of the Year'. at the
2010 MuchMusic Video Awards. The third single "
Whoa Is Me", was released on June 15, 2010, and peaked at No. 13 on the Canadian Hot 100. Over the summer, they played at festivals such as the
SCENE Music Festival, the
Ottawa Bluesfest and the
Sarnia Bayfest, where they opened for
the Black Eyed Peas. After finishing the
Streets of Gold Tour with
3OH!3, the band would "lock ourselves in the studio for a couple of months" and finish their forthcoming album. The tour was completed on November 24, 2010, at
Albuquerque,
New Mexico. They then performed at the pregame show for the
98th Grey Cup. In December, they won the 'Online Artist of the Year' at the 2010 Canadian New Media Awards. WINtour II, a cross-Canada tour that supported their upcoming album began on February 22, 2011, in
Lethbridge, Alberta and ended on March 12 in Toronto. They were nominated for two awards at the
Juno Awards of 2011,
Group of the Year and
Pop Album of the Year. The band also performed at the awards ceremony on March 27. They received four nominations at
2011 MuchMusic Video Awards, winning one for Pop Video of the Year for "Whoa Is Me". On May 12, 2011, it was announced that
hype man Kyle "Kap" Fairlie was no longer in the band, citing their reason as "6 guys going in one musical direction that didn't quite fit with the 7th." The group played at summer festivals and exhibitions including the
Red River Exhibition and
Capital Ex, where Armes' former band
the Midway State was their supporting act. The first single from their upcoming album, "
She's Dope", was released on May 23, 2011. It peaked at No. 18 on the Hot 100. "
Big Wheels" was released as the album's second single on September 9, 2011, and peaked at No. 51 on the Hot 100.
Time to Win, Vol. II was released on October 31, 2011, and reached No. 9 on the
Canadian Albums Chart. On December 20, 2011, the band released their
iTunes Session EP that included
live versions of songs from the album. In 2012, they embarked on the third edition of their WINtour.
2013–2015: Party for Your Life On March 20, 2013, the band released the single "
One in a Million". They continued opening for
Marianas Trench on the second leg of the Face The Music Tour in Canada after opening for them in the fall of 2012. On August 13, 2013, the band released the song "Party for Your Life". It was later revealed that
Party for Your Life is also the name of the upcoming album, originally scheduled for release on October 22, 2013. The album was later pushed back to January 28, 2014, to include newer material in the album. It peaked at No. 2 on the Canadian Albums Chart and was nominated for Pop Album of the Year at the
Juno Awards. Their version of "
Saturday Night" was played during the
NHL's 2013–14 season on
Hockey Night in Canada. "
Chills" was released on December 17, 2013, becoming the band's fourth single to reach the top 20 of the Canadian Hot 100 and spending 34 weeks on the chart—longer than any song they released previously. On February 9, 2014, an alternate version of "Feel So Alive" was played during the
CBC Olympic broadcasts of the
2014 Winter Olympics. The band toured from 2014, starting the fourth and final installment of their WINtour series across Canada, to opening slots in 2015 in the US. Their DJ Dave "Diggy" Ferris decided to stop touring with the group in 2014 after his girlfriend became pregnant with their first child. In the US, they joined the tours of
Hoodie Allen,
Timeflies and
Jonny Craig.
2016–present: Other projects, V and reunion In 2016, Armes released two songs that he had made with Gillett under the name Best Night Ever. Proceeds from the singles supported
Kids Help Phone and
The Trevor Project. Seja started a new project called Karter Park with original band member, Kierscey. Gillett opened up about his struggles with
mental health and created music with Armes, Martino and Hunter while maintaining his
sobriety which later became a part of an album, released under the band name Honors, titled
Feel Better (2018). During the summer of 2020, the group released the songs, "Love Is Not Enough" and "Take Us Alive" from an album called
V which was recorded back in 2015. Armes shared that
V is their final album after its
surprise release in February 2021. The band members remain active in the
music industry. Seja and Hunter signed a
publishing deal as songwriters. Hunter has also continued to release solo albums. Martino worked on Hunter's music as well as the soundtracks for the
My Little Pony web series
Tell Your Tale and television special
Bridlewoodstock. Armes produced the
scores for the
CBC series, ''
Anyone's Game and Run the Burbs''. Gillett releases music independently. Ferris is a real estate agent that djs on occasion. On April 1, 2024, Down with Webster returned and announced via social media that the band will be having a reunion tour in the summer with tour dates coming soon. The group played a handful of festivals in the summer including the
Calgary Stampede on July 9,
Ottawa Bluesfest on July 14, the Super-Spike Volleyball tournament on July 19 and 20, and the
Peterborough Musicfest on August 1. The group performed on a holiday WinTOUR tour in December 2024 and in
Hamilton in July 2025. The band played live at the
Liberal Party's victory night celebration after the
April 2025 election. The group released their first single in five years titled, "Okae" on July 30, 2025, and performed at the Boots and Hearts country music festival in
Oro-Medonte. On November 27, 2025, the band released another single titled "All Night". The song debuted at number 39 on the Canada CHR/Top 40 airplay chart. ==Members==