Windows 7 taskbar, create popup menus?

What you want to get is Jumplist Launcher. It lets you add shortcuts into the program's jumplist so you always have them available and don't have to fill your taskbar with 20 different shortcuts.

There actually is a solution to this. And it's also working in Windows 10.

I use custom menus since Windows XP (quick launch), but the current quick launch isn't friendly with subfolders. In Windows 7 you use Links instead:

Right-click windows taskbar -> Toolbars -> enable Links

Then you have to open the Links folder, it should be located somewhere here

%USERPROFILE%\Favorites\

(the best way is to create a folder in newly added Links menu and then right-click and open that folder)

Fill your folders with shortcuts, another folders, executables, songs, movies, ... whatever
You can create as many folders as you want, you can then choose which and how many of them will be shown on your taskbar (by drag'n'drop). You can also change default icons for them.

The only drawback to this is that some programs (don't know why not all) which you start from that menu will first show a popup alert if you are aware that this program can hurt your computer as this is Links folder, which was dedicated to web-related content first. (*workaround below)

The advantage of this solution is that if you create custom toolbar using other tools, you can't use those shiny custom icons for popup menus.

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EDIT: There is a workaround to disable those annoying alerts, though I recommend it only to experienced users and to those who know what they are doing with their PC as this will lessen windows security. *note that this is available only on Pro editions.

In the start menu enter gpedit.msc. Then go to User Configuration -> Administrative Templates -> Windows Components -> Attachment Manager and Add ";.exe;.lnk" to the "Inclusion list for low risk file types" setting.

7stacks might be what you seek.

7stacks

use it and love it. :)