JSFiddle - React, Tailwind, and code Playground

HTML

<script src="https://code.jquery.com/jquery-1.12.4.js"></script>
<script src="https://cdn.datatables.net/1.10.16/js/jquery.dataTables.min.js"></script>
<link rel="stylesheet" href="https://cdn.datatables.net/1.10.16/css/jquery.dataTables.min.css">
<table id="example" class="display" cellspacing="0" width="100%">
  <thead>
    <tr>
      <th>Name</th>
      <th>Position</th>
    </tr>
  </thead>
  <tbody>
    <tr>
      <td>Tiger Nixon</td>
      <td>System Architect</td>
    </tr>
    <tr>
      <td>Garrett Winters</td>
      <td>Accountant</td>
    </tr>
    <tr>
      <td>Ashton Cox</td>
      <td>Junior Technical Author</td>
    </tr>
  </tbody>
</table>

CSS

.cb-dropdown-wrap {
  max-height: 80px;
  position: relative;
  height: 219px;
  /* Temporary to fix dropdown */
}

.cb-dropdown,
.cb-dropdown li {
  margin: 0;
  padding: 0;
  list-style: none;
  transition: 0.2s 0.23s height ease-in-out;
}

.cb-dropdown {
  position: absolute;
  z-index: 1;
  width: 100%;
  height: 100%;
  overflow: hidden;
  background: white;
  border: 1px solid red;
}

.cb-dropdown-wrap:hover .cb-dropdown {
  height: 100px;
  overflow: auto;
  transition: 0.15s 0.1s height ease-in-out;
}

.cb-dropdown li.active {
  background: lightgreen;
}

.cb-dropdown li label {
  display: block;
  position: relative;
  cursor: pointer;
  line-height: 19px;
}

.cb-dropdown li label>input {
  position: absolute;
  left: 0;
  top: 0;
  width: 16px;
}

.cb-dropdown li label>span {
  display: block;
  margin-left: 24px;
  /* At least, width of the checkbox. */
  font-family: sans-serif;
  font-size: 12px;
  font-weight: normal;
  text-align: left;
}

.cb-dropdown li:hover {
  background: lightgrey;
}

table.dataTable thead .sorting,
table.dataTable thead .sorting_asc,
table.dataTable thead .sorting_desc,
table.dataTable thead .sorting_asc_disabled,
table.dataTable thead .sorting_desc_disabled {
  background-position: 100% 10px;
}

JavaScript

$(document).ready(function() {
  function cbDropdown(column) {
    return $('<ul>', {
      'class': 'cb-dropdown'
    }).appendTo($('<div>', {
      'class': 'cb-dropdown-wrap'
    }).appendTo(column));
  }

  $('#example').DataTable({
    initComplete: function() {
      this.api().columns().every(function() {
        var column = this;
        var ddmenu = cbDropdown($(column.header()))

          // -------------------------------------------------------

          .on('change', ':checkbox', function() {
            var active;
            var vals = $(':checked', ddmenu).map(function(index, element) {
              active = true;
              return $.fn.dataTable.util.escapeRegex($(element).val());
            }).toArray().join('|');

            column
              .search(vals.length > 0 ? '^(' + vals + ')$' : '', true, false)
              .draw();

            // -------------------------------------------------------
            // Highlight the current item if selected.
            if (this.checked) {
              $(this).closest('li').addClass('active');

              // If 'Select all / none' clicked ON
              if ($(this).val() === "1") {

            
                $(ddmenu).find('input[type="checkbox"]').prop('checked', this.checked)
                //$(".cb-dropdown li").prop('checked', true);
                //$('.cb-dropdown').closest('li').find('input[type="checkbox"]').prop('checked', true);
                // $('this input[type="checkbox"]').prop('checked', true);    works!
                // $( 'input[type="checkbox"]' ).prop('checked', this.checked);
                // $(this).find('input[type="checkbox"]').prop('checked', this.checked)
                //$('div.cb-dropdown-wrap.active').children().find('input[type="checkbox"]').prop('checked', this.checked)

              }
            } else // 'Select all / none' clicked OFF

            {
              $(this).closest('li').removeClass('active');
              // test if...