Down with Webster is a Canadian rap rock band from The Beaches area of Toronto who signed with Universal Motown in April 2009.

[5] 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.

[6] Following a victory at their school's "Battle of the Bands" competition,[7] the group was joined by Andrew Martino and Martin "Bucky" Seja, students from Cardinal Carter Academy for the Arts,[8][9] and other members who attended Malvern Collegiate Institute.

[10] As a jam band,[11] they made reggae,[12] funk and jazz[13] inspired music in Armes' father garage.

[14] 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.

[16] Hype man Kyle "Kap" Fairlie, a former actor whose voice work includes roles in the Nelvana series Redwall, Franklin, Babar and Rolie Polie Olie,[17] and the film The Little Bear Movie,[18] and rapper Cameron "Cam" Hunter would later join the band's lineup.

It's the reason we saved all of our money to buy albums, memorized every word, learned each chord, bass line and beat.

It's the reason we sleep in the studio and live on stage… Every show is a party and we dare the audience to have more fun than us (usually it's a tie).

[22][23] 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.

[24] In June, the group was named 'Best Unsigned Artist in Canada' by Rogers Mobile and received a recording prize worth $25,000.

[25] After facing years of rejection,[26] they captured the attention of music executives including musicians Gene Simmons and Timbaland, who wanted to sign the band to their respective record labels.

[32] The lead single from the EP "Rich Girl$", which sampled the Hall & Oates track of the same name, peaked at No.

[46] 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.

[51] 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.

On December 20, 2011, the band released their iTunes Session EP that included live versions of songs from the album.

[64][65] The band toured from 2014, starting the fourth and final installment of their WINtour series across Canada,[66] 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.

[71] Gillett opened up about his struggles with mental health[72] and created music with Armes, Martino and Hunter while maintaining his sobriety[73][74] which later became a part of an album, released under the band name Honors, titled Feel Better (2018).

[81][82] Martino worked on Hunter's music as well as the soundtracks for the My Little Pony web series Tell Your Tale[83] and television special Bridlewoodstock.

[99] Armes has cited Michael Jackson; electronic artists Justice and Skrillex; and jazz fusion musicians Stanley Clarke and Jaco Pastorious as inspirations,[100][101][102] while Gillett and Hunter has credited hip-hop groups Beastie Boys, Wu-Tang Clan and Cypress Hill; and rock bands Aerosmith,[103] Rage Against the Machine and Led Zeppelin for helping the band shape their blend of music.