Program bypasses some code

[passel]

As DataMiser says, you can add songs to a MediaPlayer PlayList and it will play the songs itself.

<edit> I added the below before looking at your code and realizing that you are adding songs apparently to the playlist. I would assume you just need to start playing the first item and it should continue on automatically. If you want to read how I did it without using the builtin playlist you can continue reading
</edit>
<edit2>
I see that the above edit was was DataMiser surmised as well in his post. I should have read a little further before posting.
</edit2>

But, as my VB6 code was originally written for the earlier version of MediaPlayer (around 15 years ago) which didn't have a playlist, I never got around to working with the built in playlist with the newer version of MediaPlayer (i.e. one available for the last 12 years or so). I maintained my own list and based on using the PlayStateChanged event to detect when a song was fininished and starting the next song.
I'm now on the machine with more of my old VB6 code, so I'll take a look at what I did.

  Const PLAYSTATE_Stopped = 1
  Const PLAYSTATE_Paused = 2
  Const PLAYSTATE_Playing = 3
  Const PLAYSTATE_MediaEnded = 8

  'added for new WMP
  Dim DequeueASong As Boolean


Private Sub MediaPlayer1_PlayStateChange(ByVal NewState As Long)
'I had other states in the case, but aren't currently needed
    Select Case NewState
      Case PLAYSTATE_MediaEnded
        DequeueASong = True
    End Select
End Sub

Private Sub Timer1_Timer()
  If DequeueASong Then
    DequeueASong = False
    Play_Next_Song
  End If
End Sub

The above is the crux of the code. The Call to sub Play_Next_Song is where I chose the next song to be played and loaded it. There was a lot of code in there using various indexes and calling other subs so I didn't bother posting it because it depends on a user defined type and other mechanisms that would just complicate things. You should be able to just keep track of which song you played from your list and start the next one.

The reason it sets a flag in the PlayStateChange event and has code in the timer to start the next song is because starting a new song in the PlayStateChange event causes a PlayStateChange event and that seemed to corrupt the process somehow and the new song ended up not starting. Setting the flag and leaving the event, and then starting the song at the next timer tick, prevented that failure.

p.s. The code has the comment "added for new WMP" referring to the boolean because the original Windows Media Player had a SongEnded event, and you could start a new song in that event without problem. The "new" WMP doesn't have the event any longer, or doesn't trigger it, and couldn't start a new song within the new event, so the boolean was added.