Initial, a crezut ca nu are nici o sansa. Ceilalti baieti – Gary Barlow, Mark Owen, Jason Orange, Howard Donald – erau prea cuminti in comparatie cu el. „Take That s-a nascut in 1990, la initiativa managerului Martin Nigel Smith, care isi dorea sa creeze o trupa de baieti, care sa-i concureze pe cei de la „New Kids On The Block. Robbie nu s-a adaptat imediat la cerintele formatiei. Avea probleme cu pasii de dans, dar, in cele din urma, cu putin efort a devenit unul dintre cei mai buni dansatori din trupa. Primul single al formatiei s-a numit „Do What U Like. Cu un videoclip in care cei cinci isi aratau posterioarele goale, baietii au fost banuiti ca au alte orientari sexuale. Au dat lovitura in topuri cu piesa „It Only Takes a Minute declansand o isterie in randul fanelor, comparabila cu Beatlesmania.
Succesul i s-a urcat la cap lui Robbie care a devenit o „oaie neagra a formatiei. Acesta a fost avertizat in repetate randuri de managerul „Take That sa-si revizuiasca atitudinea, sa renunte la consumul excesiv de alcool si la aparitiile alaturi de membrii „Oasis care aveau o reputatie foarte proasta. |n 1995, managerul Martin Nigel Smith i-a cerut lui Robbie sa paraseasca formatia, desi oficial Robbie a declarat ca motivul plecarii este dorinta de a incepe o cariera solo. La scurt timp dupa plecarea lui, mai multe fane au amenintat ca se vor sinucide, iar membrii formatiei „Take That au lansat pe piata o noua varianta a albumului „Nobody Else, care continea piese fara vocea lui Robbie. „How Deep Is Your Love a fost ultima piesa „Take That si singura care nu contine vocea lui Robbie.
Dupa ce a parasit „Take That, Robbie si-a schimbat radical imaginea. A cantat in deschiderea concertului trupei Oasis din Glastonbury, cu parul decolorat, cu dintii vopsiti cu negru, nebarbierit, imbracat saracacios si mai gras cu 18 kilograme, fapt ce l-a determinat pe Noel Gallagher sa se refere la el astfel: „Acel dansator gras de la «Take That».
Primul single din cariera solo a lui Robbie a fost un cover dupa melodia „Freedom 90 a lui George Michael, lansat in 1996. Robbie s-a clasat pe locul doi in topurile din Marea Britanie cu aceasta piesa, dar la scurt timp a fost inclus intr-un program de reabilitare la clinica „Clouds House Drink and Drug Rehabilitation.
A revenit in 1997, lansand un al doilea single, „Old Before I Die si un nou album solo, „Life Thru Lens, inspirat din viata sa. Single-ul „Angels, scris de catre Guy Chambers avea sa-i relanseze cariera muzicala. Balada a propulsat albumul pe locul I in topuri si a fost votata cel mai bun cantec din ultimii 25 de ani de catre ascultatorii postului de radio BBC, primind si un premiu special la cea de-a 25-a editie a ceremoniei „Brit Awards care a avut loc in februarie 2005. Cel de-al doilea album al lui Robbie, „Ive Been Expecting You din 1998 ramane inca cel mai bine vandut album din cariera sa (2, 7 milioane de exemplare).
In anul 2000, albumul „Sing When Youre Winning l-a ajutat pe Robbie sa-si consolideze pozitia de cel mai bun solist pop al lumii, dar totodata i-a creat si o imagine controversata. In videoclipul melodiei „Rock DJ Robbie aparea nud, apoi se transforma intr-un schelet. Chiar daca a fost nominalizat la MTV Video Music Awards, videoclipul, o combinatie de nuditate si violenta, a starnit reactia negativa a publicului, iar scena a fost cenzurata de majoritatea posturilor de televiziune.
De atunci, Robbie si-a construit o adevarata reputatie de a aparea dezbracat in fotografii, videoclipuri si concerte live.
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