Open Frequent Files (in addition to Open Recent Files). Seems easy enough to me. GUI file browsing details that influence the width of their column. Too often I find long names truncated and have to adjust the width myself when there's obviously lots of white space in other columns. Maybe a bit too OS for your question.
If you use Everything on windows you can sort by run count to list the most run files at the top, which is an approximation of what you want.
I was thinking more integrated into any particular program. Also, I'm on Linux mostly. But yea, that looks cool