- Right-click on taskbar
- Go to Properties
- On Properties → Start Menu tab (in Windows 8, it is called Jump Lists)
- Check Store and display a list of recently opened programs under Privacy.
The location of this setting has changed in Windows 10.
- Open the Start menu
- Select Settings
- Select the Personalization button
- Select Start in the left column
- Toggle Show most used apps to the On position
In Windows 10 Pro, below option need to be enabled.
Settings > Privacy > General >
Let Windows track app launches to improve Start and search results