The accompanying music video features Drake and Songz venturing off into Toronto nightlife, interspersed with contemplative scenes.

[2] The song was first released as Drake's follow-up track to "Best I Ever Had" for his So Far Gone mixtape, with Trey Songz and Lil Wayne received featuring credits.

[3] After the success of the two singles, Drake decided to release a retail version of the mixtape in the form of an extended play, including the song.

"[3] In an interview with MTV News, Drake explained how the song came about, stating, "It has this pocket, and there was no melody yet.

I remember [producer Noah '40' Shebib] kind of making the joint, and then he hit this sound, which is the chords that are in there.

[1] Songz said that Drake originally called him on advice of segueing his singing into rapping on interludes, then the terms of what records he would be featured on the mixtape, as he sent him the "Successful" track.

"[1] Shaheem Reid of MTV News said this about the song: "Trey Songz's hook expresses the dreams of a young black male coming from nothing to something, and Drake's raps put the hip-hop nation on notice, while conveying his own desperation and hope and revealing family struggles.

Let's not forget Lil Wayne's magnificent at bat as cleanup hitter..."[1] An "endearing and revealing" moment happens in the record when Drake refers to an incident when his mother contemplated leaving home during family troubles.

[1] The music video for the Ready version of the song, filmed in Drake's hometown of Toronto, Ontario, was directed by Jake White.

"[10] The video begins with Drake going up an elevator while Songz sings shirtless on the edge of a bed with a woman laying naked on the other side looking on.

"[10]- Barack ObamaSongz and Drake performed the song on 106 & Park on September 2, 2009, as a part of a medley of "I Need a Girl" and "LOL Smiley Face.

"[11] The song was remixed and renamed "Stressful" by Joell Ortiz & Novel for their critically acclaimed mixtape Defying the Predictable.

In January 2010, nearly a year after the release of the song, an alternate version of Drake's 3rd verse leaked online.

[14] Andrew Rennie of Now Magazine called a "cautionary anthem" and the song the top track on the album.

[15] Rennie also said that "Successful" and "Black Roses", showcase Songz's developed, more mature side.

[15] Sean Fennessey of The Village Voice said, "The calm, yearning song is a bona fide hit, and also the best example of where r&b lives today.

"[17] Shaheem Reid of MTV News said, "It's not a record that will kill the clubs, but when you just want to listen to superb lyricism and enthralling harmony, it's a must have.