איוב, פרק כ״א, פסוק ל״ג

The peace and prosperity that accompany a wicked person throughout life often do not abandon him in his final moments. Even in death and burial, he is granted comfort and immense honor. He is laid to rest in a prime, carefully chosen location, covered by the soft earth of a valley or a gentle plain [מצודת ציון, רלב״ג, אבן עזרא]. The primary approach among commentators is that because the wicked individual grew so accustomed to a life of ease and luxury, he anticipates that even his time in the grave will be sweet and pleasant [מצודת דוד, אלשיך].

Beyond the physical burial site, there are varying perspectives on the massive crowds associated with his passing. One approach views this as a magnificent, royal funeral procession reserved for the great and important. Countless people walk ahead of the coffin to prepare the burial, while multitudes are drawn to walk behind the bier to escort him. Comforted by the anticipation of this grand display of honor, the wicked person becomes arrogant, completely ignoring the impending judgment and punishment of hell that awaits him [מצודת דוד, אלשיך].

Alternatively, this imagery represents the universal cycle of human life and death. The individual understands that his fate is shared by all humanity, finding solace in the fact that countless people have already died before him, and all others will eventually follow him to the grave [אבן עזרא, ביאור שטיינזלץ]. A similar view suggests he finds comfort within his own family circle, knowing his ancestors are already there waiting for him, and his children will eventually join him [רמב״ן]. Finally, another approach interprets these masses not as funeral escorts or deceased generations, but as the living—the many people who are drawn to follow in his evil footsteps and adopt his wicked schemes [רש״י].