Duba wurin da ke ƙasa sannan ka amsa tambayar daga baya a cikin harshe ɗaya kamar yadda wurin yake:  Passage: Grey ya rubuta "Done With Like" da "She Said", tare da Jon Ingoldsby da kuma 'yar wasan Amurka Brie Larson, don kundi na farko da kawai na Larson, A ƙarshe Daga P.E. (2005). A shekara ta 2005, Grey ya kasance a cikin waƙoƙin ƙungiyar hip hop ta Amurka Fort Minor, "Where'd You Go" da "Be Somebody". An saki "Where'd You Go" a matsayin guda a ranar 14 ga Afrilu, 2006, tare da bidiyon kiɗa mai biyo baya ba da daɗewa ba. Waƙar ta sami nasarar kasuwanci kuma ta ƙare ta zama ta huɗu a saman Amurka Billboard Hot 100 ginshiƙi kuma ta zama platinum ta Recording Industry Association of America (RIAA). Bayan ta yi aiki tare da mai shirya kiɗa Jonathan Ingoldsby, Grey ta fitar da kundin waƙarta na farko, mai suna Like Blood Like Honey, a ranar 6 ga Yuni, 2006, a ƙarƙashin Warner Bros. Records. Kundin ya kai matsayi na 35 a kan Billboard's Heatseekers Albums chart. A wannan lokacin, Grey ya sauka wuraren buɗewa don yawon shakatawa tare da Jamie Cullum, k.d. lang, Daniel Powter, Teddy Geiger da Duncan Sheik. Ta hanyar haɗin ta daga Machine Shop Records, Grey ya zama kusa da haɗin Linkin Park Styles of Beyond da Apathy. Har ma an nuna ta a waƙoƙi biyu mai taken "Victim" da "No Sad Tomorrow", daga kundin faifan studio na biyu na Apathy, Wanna Snuggle? (2009). Grey ya yi yawon shakatawa a matsayin wani ɓangare na ƙungiyar Duncan Sheik kuma ya ba da gudummawa sosai ga kundin waƙarsa na 2009, Whisper House. A shekara ta 2009, Grey ya bayyana a matsayin mai goyon bayan mawaƙa a kan kundi na farko na Yohanna, Butterflies da Elvis. A watan Agusta 2009, har yanzu a karkashin sunan Holly Brook, ta ba da waƙar ta "It's Raining Again" da hotonta zuwa kamfen na talla don Ciao Water. A farkon 2010, ta yi a cikin gidan wasan kwaikwayo na "Whisper House", tana wasa ɗaya daga cikin manyan mawaƙa biyu, tare da David Poe. A ranar 10 ga Yuni, 2010, ta fitar da kanta ta fito da waƙoƙi bakwai (EP), O<unk>Dark: talatin. Duncan Sheik da Jon Ingoldsby ne suka yi aikin samar da EP din.  Tambaya: A wace rana ta saki O'Dark: talatin?
Ranar 10 ga watan Yuni, 2010,