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In 2013, Weiss participated in the tenth season of the German talent show ''[[Deutschland sucht den Superstar]]'', the German adaptation of the [[Idol series|''Idol'' franchise]].<ref>[https://www.rtl.de/cms/dsds-2013-kandidat-wincent-weiss-mit-dem-gewissen-etwas-im-recall-1381400.html rtl.de] Wincent Weiss 2013 - DSDS</ref> After a successful audition, he became one of the top 29 contestants but failed to make it to the live shows.<ref name="focus">{{cite web|url=https://www.focus.de/kultur/musik/wincent-weiss-dieter-bohlens-dsds-abfuhr-war-das-beste-was-dem-saenger-passieren-konnte_id_7151437.html|title=Dieter Bohlens "DSDS"-Abfuhr war das Beste, was dem Sänger passieren konnte|website=Focus.de|language=de|access-date=24 May 2018}}</ref> In 2015, German DJ duo [[Gestört aber GeiL]] and Koby Funk produced a remix of his rendition of "Unter meiner Haut", an acoustic [[cover version|cover]] of [[Elif Demirezer]]'s same-titled song which Weiss had previously uploaded on [[YouTube]].<ref name="focus"/> The song peaked as number six on the [[German Singles Chart]] and earned a platinum certification by the [[Bundesverband Musikindustrie]] (BVMI).<ref name="focus"/>
Before he received his first record deal, he was a waiter and a model. He has been represented by Tune Models in Cologne. During the fashion week for the spring/summer 2016-season, he walked as an exclusive for [[Versace]] menswear.<ref>[https://tune-models.com/collection.php?id=134 Tune Models. Retrieved 2021-04-12.]</ref>
Weiss's first solo single "Regenbogen" was released the same year but failed to chart. In 2016, he released the single "[[Musik sein]]", which was a success in the German-speaking part of Europe, becoming a top ten hit in Austria and Switzerland. Follow-up "[[Feuerwerk (song)|Feuerwerk]]", released in 2017, entered the top thirty in Germany and Switzerland and preceded his first studio album ''[[Irgendwas gegen die Stille]]'', released in April 2017. A commercial success, it peaked at number three in Germany and at number four in Switzerland, eventually going platinum in both countries.<ref name=ger/> A reissue of the album was released later that year.<ref name="focus"/> In May 2017, Weiss served as a member of Germany's jury at the [[Eurovision Song Contest 2017|62nd Eurovision Song Contest]] in [[Kyiv, Ukraine]].<ref name="focus"/> In November, he was awarded the [[MTV Europe Music Award for Best German Act]].<ref name="focus"/>
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