Ok, it was hard to find clues without giving away too much, so maybe some are very easy and others slightly harder. I can always give extra clues later for the latter.
Clues For Video
#1: This recent single got some controversy in the beginning of release. A comeback from this artist on the European charts and written by a 2016 Grammy winner.
#2: This huge and very quotable hit, was the breakthrough of this artist in international markets. Covered many times and was nominated for 2 Grammy's. The latest album was maybe not so commercially successful, but highly praised (also on atrl)
#3: This group's first number 1 single in the country they are based in. The video has two versions, the latter being a tribute to a character leaving a very popular show over there.
#4: This global hit, was originally not meant for this artist, but became the artist's highest peaking song on the billboard hot 100.
#5: The 3rd single after two globally successful singles from this group, one even a top 10 hit in the US. The video stars another star of a very popular series. I say another, because one of her co-stars, was already in a previous video we did.
#6: This signature song is still very remembered, even if the artist is not really active right now. The single became a huge global hit and the video was at the time one of the most successful video's on youtube.
#7: This dance pop song, became the first top 10 hit of this group and of the guest on this single. The guest was no other than Queen B, but maybe not the one you think
#8: Very recent and the artist is not the only celeb in the video
#9: The signature song of this artist. A huge and global hit and in all definitions a classic. Became a famous internet meme.
#10:The second single of this socialite's first album, which contains vocals from a then still unknown singer, but know very known for many hits but also recent months/years for something else
#11: A yearly returning anthem for a very recent holiday
#12: This group's lead single from their 4th album, became one of their signature songs. It also became a huge hit in Europe and the screenshot says a lot about the title of this song.
#13: The first real single for the 'comeback' of this artist, who is probably seen as one of the laziest artists right now. The video has two versions, the latter because of the fan's.
#14: Was originally recorded by another artist, who was not really happy about this release. The video is in black and white and was part of a very successful dual release. Was released in 2008 btw.
#15: First solo adventure in three years for this artist, the official video has less views on Youtube than another version.
#16: I'm gonna ask Marn/ Denis Stoff to fill this further in, because I have no idea
This metal band's final single from their 4th album, the video stars the lead vocalist of another metal band.
don't want it too easy or too hard... may take a bit to think of videos 
Loving all the throwbacks